tert-Butyl methyl ether → 3-Chloro-4,7-difluoro-benzo[b]thiophene-2-carboxylic acid (2-ethyl-5-pyridin-4-yl-benzyl)-(4-methylamino-cyclohexyl)-amide dihydrochloride

HRID 2389699Notes

Reaction equation

HRID 2389699 reaction equation
[Cl:1][C:2]1[C:3]2[C:43]([F:44])=[CH:42][CH:41]=[C:40]([F:45])[C:4]=2[S:5][C:6]=1[C:7]([N:9]([CH2:25][C:26]1[CH:31]=[C:30]([C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)[CH:29]=[CH:28][C:27]=1[CH2:38][CH3:39])[CH:10]1[CH2:15][CH2:14][CH:13]([N:16](C)[C:17](=O)OC(C)(C)C)[CH2:12][CH2:11]1)=[O:8].CC(OC)(C)C>C(Cl)Cl>[ClH:1].[ClH:1].[CH2:38]([C:27]1[CH:28]=[CH:29][C:30]([C:32]2[CH:33]=[CH:34][N:35]=[CH:36][CH:37]=2)=[CH:31][C:26]=1[CH2:25][N:9]([CH:10]1[CH2:15][CH2:14][CH:13]([NH:16][CH3:17])[CH2:12][CH2:11]1)[C:7]([C:6]1[S:5][C:4]2[C:40]([F:45])=[CH:41][CH:42]=[C:43]([F:44])[C:3]=2[C:2]=1[Cl:1])=[O:8])[CH3:39]

Participants

4

Reactant 2

HCID 15413tert-Butyl methyl etherHCID 59683611tert-Butyl {4-[(3-chloro-4,7-difluoro-benzo[b]thiophene-2-carbonyl)-(2-ethyl-5-pyridin-4-yl-benzyl)-amino]-cyclohexyl}-methyl-carbamate

Product 1

HCID 683145813-Chloro-4,7-difluoro-benzo[b]thiophene-2-carboxylic acid (2-ethyl-5-pyridin-4-yl-benzyl)-(4-methylamino-cyclohexyl)-amide dihydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl carbamate 238 (40 mg, 0.06 mmol) is deprotected using Method F. The isolated salt is then dissolved in the minimum amount of DCM and added dropwise to cold (0° C.) TBME (5 mL). The resultant precipitate is isolated by filtration and dried to afford the title compound.

Sources & evidence

ORD record
ord-987adcb4bc7d4ce2a042885a305597e2
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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