Water → HCID 178488013, compound

HRID 1007308Notes

Reaction equation

HRID 1007308 reaction equation
C(N(CC)C(C)C)(C)C.[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][CH:12]=1.[C:20]([O:24][C:25]([NH:27][C:28]([NH:37][C@@H:38]1[CH2:43][CH2:42][CH2:41][CH2:40][C@@H:39]1[NH:44][C:45]1[C:54]2[C:49](=[CH:50][CH:51]=[C:52]([O:55][CH3:56])[CH:53]=2)[N:48]=[C:47]([NH2:57])[N:46]=1)=[N:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:26])([CH3:23])([CH3:22])[CH3:21].O>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:33]([O:32][C:30]([NH:29][C:28]([NH:37][C@@H:38]1[CH2:43][CH2:42][CH2:41][CH2:40][C@@H:39]1[NH:44][C:45]1[C:54]2[C:49](=[CH:50][CH:51]=[C:52]([O:55][CH3:56])[CH:53]=2)[N:48]=[C:47]([NH:57][C:15](=[O:16])[C:14]2[CH:18]=[CH:19][C:11]([Cl:10])=[CH:12][CH:13]=2)[N:46]=1)=[N:27][C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26])=[O:31])([CH3:34])([CH3:35])[CH3:36]

Participants

7

Reactant 4

HCID 962WaterHCID 85014-Chlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 178488017HCID 178488017, compound

Product 1

HCID 178488013HCID 178488013, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 366 mg of N,N-diisopropylethylamine in 10 mL of methylene chloride was combined with 60 mg of 4-dimethylaminopyridine and 0.156 mL of 4-chlorobenzoyl chloride. This was treated dropwise with a solution of 500 mg of (1R,2S)-N-[N,N′-bis(tert-butoxycarbonyl)]amidino-2-(2-amino-6-methoxyquinazolin-4-yl)aminocyclohexylamine in 10 mL of methylene chloride, and stirred at room temperature for 3 hours. The reaction solution was combined with water, extracted with methylene chloride, and dried. After the solvent was distilled off, the residue was purified by column chromatography on silica gel (chloroform:methanol=30:1) to obtain 560 mg of the desirable compound.

Workup

  1. extractionextracted with methylene chloride
  2. customdried
  3. distillationAfter the solvent was distilled off
  4. customthe residue was purified by column chromatography on silica gel (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-73f05044f3e34625bf0c8c86d4582965
Source dataset
uspto-grants-2004_09
Patent number
US06794389B2

Reaction notes

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