6-amino-5-methoxy-1,3-benzothiazol-2(3H)-one → (RS)-N-Butyl-N-(cyanomethyl)-4-[(5-methoxy-2-oxo-2,3-dihydro-1,3-benzothiazol-6-yl)amino]-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxamide

HRID 930984Notes

Reaction equation

HRID 930984 reaction equation
[CH2:1]([N:5]([CH2:22][C:23]#[N:24])[C:6]([CH:8]1[CH2:13][CH2:12][C:11]2[C:14]3[C:19](Cl)=[N:18][CH:17]=[N:16][C:15]=3[S:21][C:10]=2[CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4].[NH2:25][C:26]1[C:35]([O:36][CH3:37])=[CH:34][C:29]2[NH:30][C:31](=[O:33])[S:32][C:28]=2[CH:27]=1>>[CH2:1]([N:5]([CH2:22][C:23]#[N:24])[C:6]([CH:8]1[CH2:13][CH2:12][C:11]2[C:14]3[C:19]([NH:25][C:26]4[C:35]([O:36][CH3:37])=[CH:34][C:29]5[NH:30][C:31](=[O:33])[S:32][C:28]=5[CH:27]=4)=[N:18][CH:17]=[N:16][C:15]=3[S:21][C:10]=2[CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 900149486-amino-5-methoxy-1,3-benzothiazol-2(3H)-oneHCID 90015777(RS)-N-butyl-4-chloro-N-(cyanomethyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxamide

Product 1

HCID 90014553(RS)-N-Butyl-N-(cyanomethyl)-4-[(5-methoxy-2-oxo-2,3-dihydro-1,3-benzothiazol-6-yl)amino]-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxamide

Procedure

100 mg (276 μmol) (RS)—N-butyl-4-chloro-N-(cyanomethyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxamide (prepared according to intermediate example 88a) were transformed in analogy to example 1 using 6-amino-5-methoxy-1,3-benzothiazol-2(3H)-one to give after working up and purification 15.9 mg (10%) of the title compound.

Workup

  1. customto give
  2. custompurification 15.9 mg (10%) of the title compound

Sources & evidence

ORD record
ord-4cb5293a91f849a8a0fa359d4d711379
Source dataset
uspto-grants-2016_03
Patent number
US09296757B2

Reaction notes

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