Hydrochloric Acid → HCID 90221442, compound

HRID 1481931Notes

Reaction equation

HRID 1481931 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([O:89][CH3:90])=[C:7]2[CH2:12][N:13]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]([C:24](=[O:73])[C:25]2[CH:30]=[CH:29][C:28]([C:31]([N:33]3[C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=4[N:37]([CH2:44][C:45]4[C:54]5[C:49](=[C:50]([Br:55])[CH:51]=[CH:52][CH:53]=5)[CH:48]=[CH:47][C:46]=4[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]3)=[O:32])=[CH:27][CH:26]=2)[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].[ClH:91]>O1CCOCC1>[ClH:91].[ClH:91].[Br:55][C:50]1[CH:51]=[CH:52][CH:53]=[C:54]2[C:49]=1[CH:48]=[CH:47][C:46]([O:56][CH3:57])=[C:45]2[CH2:44][N:37]1[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[N:33]([C:31](=[O:32])[C:28]2[CH:27]=[CH:26][C:25]([C:24]([N:17]3[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[N:13]([CH2:12][C:7]4[C:8]5[C:3](=[C:2]([Br:1])[CH:11]=[CH:10][CH:9]=5)[CH:4]=[CH:5][C:6]=4[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]3)=[O:73])=[CH:30][CH:29]=2)[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]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118677389HCID 118677389, compound

Product 1

HCID 90221442HCID 90221442, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl N-[(1S)-2-[[(3S)-5-[(5-bromo-2-methoxy-1-naphthyl)methyl]-1-[4-[(3S)-5-[(5-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 (50 mg, 0.037 mmol) in dioxane (1 mL) at 0° C. was added 4 M HCl in dioxane (0.6 mL) dropwise and the cooling bath removed. After 3 h the mixture was evaporated and the residue was triturated with hexane to afford the title compound (35 mg, 77.2%) as a white solid. LC-MS: 1153.2 (M+H).

Workup

  1. customthe cooling bath removed
  2. customAfter 3 h the mixture was evaporated
  3. customthe residue was triturated with hexane

Sources & evidence

ORD record
ord-736df64887634eebae54f3a9e33e6c29
Source dataset
uspto-grants-2016_08
Patent number
US09409888B2

Reaction notes

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