Hydrochloric Acid → (2S)-N-[(3S)-5-[(6-Bromo-2-methoxy-1-naphthyl)methyl]-1-[3-[(3S)-5-[(6-bromo-2-methoxy-1-naphthyl)methyl]-3-[[(2S)-2-(methylamino)propanoyl]amino]-4-oxo-2,3-dihydro-1,5-benzodiazepine-1-carbonyl]benzoyl]-4-oxo-2,3-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide dihydrochloride

HRID 1481929Notes

Reaction equation

HRID 1481929 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH2:12][N:13]1[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]([C:24](=[O:73])[C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([N:33]4[C:39]5[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=5[N:37]([CH2:44][C:45]5[C:54]6[C:49](=[CH:50][C:51]([Br:55])=[CH:52][CH:53]=6)[CH:48]=[CH:47][C:46]=5[O:56][CH3:57])[C:36](=[O:58])[C@@H:35]([NH:59][C:60](=[O:72])[C@@H:61]([N:63](C(OC(C)(C)C)=O)[CH3:64])[CH3:62])[CH2:34]4)=[O:32])[CH:26]=3)[CH2:16][C@H:15]([NH:74][C:75](=[O:87])[C@@H:76]([N:78](C)[C:79](=O)OC(C)(C)C)[CH3:77])[C:14]1=[O:88])=[C:7]([O:89][CH3:90])[CH:6]=[CH:5]2.[ClH:91]>O1CCOCC1>[ClH:91].[ClH:91].[Br:55][C:51]1[CH:50]=[C:49]2[C:54](=[CH:53][CH:52]=1)[C:45]([CH2:44][N:37]1[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[N:33]([C:31](=[O:32])[C:27]3[CH:28]=[CH:29][CH:30]=[C:25]([C:24]([N:17]4[C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=5[N:13]([CH2:12][C:8]5[C:9]6[C:4](=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=6)[CH:5]=[CH:6][C:7]=5[O:89][CH3:90])[C:14](=[O:88])[C@@H:15]([NH:74][C:75](=[O:87])[C@@H:76]([NH:78][CH3:79])[CH3:77])[CH2:16]4)=[O:73])[CH:26]=3)[CH2:34][C@H:35]([NH:59][C:60](=[O:72])[C@@H:61]([NH:63][CH3:64])[CH3:62])[C:36]1=[O:58])=[C:46]([O:56][CH3:57])[CH:47]=[CH:48]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118677424tert-butyl N-[(1S)-2-[[(3S)-5-[(6-bromo-2-methoxy-1-naphthyl)methyl]-1-[3-[(3S)-5-[(6-bromo-2-methoxy-1-naphthyl)methyl]-3-[[(2S)-2-[tert-butoxycarbonyl(methyl)amino]propanoyl]amino]-4-oxo-2,3-dihydro-1,5-benzodiazepine-1-carbonyl]benzoyl]-4-oxo-2,3-dihydro-1,5-benzodiazepin-3-yl]amino]-1-methyl-2-oxo-ethyl]-N-methyl-carbamate

Product 1

HCID 90221011(2S)-N-[(3S)-5-[(6-Bromo-2-methoxy-1-naphthyl)methyl]-1-[3-[(3S)-5-[(6-bromo-2-methoxy-1-naphthyl)methyl]-3-[[(2S)-2-(methylamino)propanoyl]amino]-4-oxo-2,3-dihydro-1,5-benzodiazepine-1-carbonyl]benzoyl]-4-oxo-2,3-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide dihydrochlorideYield 58.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of tert-butyl N-[(1S)-2-[[(3S)-5-[(6-bromo-2-methoxy-1-naphthyl)methyl]-1-[3-[(3S)-5-[(6-bromo-2-methoxy-1-naphthyl)methyl]-3-[[(2S)-2-[tert-butoxycarbonyl(methyl)amino]propanoyl]amino]-4-oxo-2,3-dihydro-1,5-benzodiazepine-1-carbonyl]benzoyl]-4-oxo-2,3-dihydro-1,5-benzodiazepin-3-yl]amino]-1-methyl-2-oxo-ethyl]-N-methyl-carbamate (15 mg, 0.01 mmol) in dioxane (0.2 mL) at 0° C. was added 4 N HCl in dioxane (0.2 mL), the cooling bath was removed and the mixture was stirred at RT. After 2 h, the mixture was evaporated to provide the title compound (8 mg, 58.9%) as an off white solid. LC-MS: 1153.6 (M+H).

Workup

  1. customthe cooling bath was removed
  2. customthe mixture was evaporated

Sources & evidence

ORD record
ord-afabb9b042dd428ba5981f366d48f8ca
Source dataset
uspto-grants-2016_08
Patent number
US09409888B2

Reaction notes

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