Hydrochloric Acid → HCID 67681756, compound

HRID 1751350Notes

Reaction equation

HRID 1751350 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:52]([CH3:54])[CH3:53])[C:7]([N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]1[NH:15][C:16]([C:19]2[CH:20]=[C:21]3[C:33]4[C:34]5[C:24](=[CH:25][C:26]([C:35]6[NH:39][C:38]([C@@H:40]7[CH2:44][CH2:43][CH2:42][N:41]7C(OC(C)(C)C)=O)=[N:37][CH:36]=6)=[CH:27][C:28]=5[CH2:29][CH2:30][C:31]=4[CH:32]=2)[CH2:23][CH2:22]3)=[CH:17][N:18]=1)=[O:8])=[O:4].Cl.[CH3:56][O:57][C:58]([NH:60][C@@H:61]([CH:65]1[CH2:70][CH2:69][O:68][CH2:67][CH2:66]1)[C:62]([OH:64])=O)=[O:59].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:52]([CH3:54])[CH3:53])[C:7]([N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]1[NH:15][C:16]([C:19]2[CH:32]=[C:31]3[C:33]4[C:34]5[C:28](=[CH:27][C:26]([C:35]6[NH:39][C:38]([C@@H:40]7[CH2:44][CH2:43][CH2:42][N:41]7[C:62](=[O:64])[C@@H:61]([NH:60][C:58](=[O:59])[O:57][CH3:56])[CH:65]7[CH2:70][CH2:69][O:68][CH2:67][CH2:66]7)=[N:37][CH:36]=6)=[CH:25][C:24]=5[CH2:23][CH2:22][C:21]=4[CH:20]=2)[CH2:29][CH2:30]3)=[CH:17][N:18]=1)=[O:8])=[O:4]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59264488(S)-2-(Methoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetic acidHCID 69675359HCID 69675359, compound

Product 1

HCID 67681756HCID 67681756, compoundYield 26.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (S)-tert-butyl 2-(5-(7-(2-((S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)-4,5,9,10-tetrahydropyren-2-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (55 mg, 0.08 mmol) in DCM (3 mL) was added HCl (4M in dioxane, 0.25 mL). The solution stirred for 1 h, and the solvent was removed. The intermediate was dissolved in DMF (2 mL). (S)-2-(methoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetic acid (16 mg, 0.08 mmol), HATU (29 mg, 0.08 mmol), and DIPEA (0.06 mL, 0.37 mmol) were added sequentially. The solution was stirred o/n and the mixture was purified by HPLC to yield product (17.9 mg). LCMS-ESI+: calc'd for C46H56N8O7: 832.99 (M+); Found: 833.25 (M+H+).

Workup

  1. customthe solvent was removed
  2. dissolutionThe intermediate was dissolved in DMF (2 mL)
  3. stirringThe solution was stirred o/n and the mixture
  4. customwas purified by HPLC

Sources & evidence

ORD record
ord-82b00d94ad574e589ce85f670554435f
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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