Water → HCID 178423421, compound

HRID 2237602Notes

Reaction equation

HRID 2237602 reaction equation
C(N(CC)C(C)C)(C)C.[S:10]1[C:14]([C:15]([Cl:17])=[O:16])=[CH:13][C:12]2[CH:18]=[CH:19][CH:20]=[CH:21][C:11]1=2.[NH2:22][C:23]1[N:32]=[C:31]([NH:33][C@H:34]2[CH2:39][CH2:38][CH2:37][CH2:36][C@H:35]2[NH:40][C:41]([NH:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])=[N:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([CH3:58])[CH:29]=2)[N:24]=1.O>C(Cl)Cl.CN(C)C1C=CN=CC=1>[ClH:17].[ClH:17].[C:54]([O:53][C:51]([NH:50][C:41]([NH:40][C@@H:35]1[CH2:36][CH2:37][CH2:38][CH2:39][C@@H:34]1[NH:33][C:31]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([CH3:58])[CH:29]=2)[N:24]=[C:23]([NH:22][C:15]([C:14]2[S:10][C:11]3[CH:21]=[CH:20][CH:19]=[CH:18][C:12]=3[CH:13]=2)=[O:16])[N:32]=1)=[N:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])=[O:52])([CH3:55])([CH3:56])[CH3:57]

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 142384Benzo[b]thiophene-2-carbonyl ChlorideHCID 178423436HCID 178423436, compound

Product 1

HCID 178423421HCID 178423421, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a 604 mg of N,N-diisopropylethylamine in 4 ml of methylene chloride, 10 mg of 4-dimethylaminopyridine and 613 mg of benzo[b]thiophene-2-carbonylchloride were added, and the mixture was stirred for 60 minutes. To the mixture was added dropwise a solution of 800 mg of N-{(1R,2S)-2-[(2-amino-6-methylquinazolin-4-yl)amino]cyclohexyl}-N′,N″-bis(tert-butoxycarbonyl)guanidine obtained in Reference Example 1 in 5 ml of methylene chloride, followed by stirring at room temperature for 15 hours. The reaction solution was mixed with water, extracted with methylene chloride and then dried. The solvent was distilled off and the residue was purified by silica gel column chromatography (chloroform:methanol=30:1) to obtain 890 mg of the desirable compound.

Workup

  1. stirringby stirring at room temperature for 15 hours
  2. extractionextracted with methylene chloride
  3. customdried
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by silica gel column chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-63be15fe66ff47ba8bab703d38e9e09d
Source dataset
uspto-grants-2010_05
Patent number
US07718663B2

Reaction notes

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