6-amino-5-methoxy-1,3-benzothiazol-2(3H)-one → (RS)-N-Ethyl-N-(2-methoxyethyl)-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 930988Notes

Reaction equation

HRID 930988 reaction equation
Cl[C:2]1[C:3]2[C:10]3[CH2:11][CH2:12][CH:13]([C:15]([N:17]([CH2:22][CH3:23])[CH2:18][CH2:19][O:20][CH3:21])=[O:16])[CH2:14][C:9]=3[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:24][C:25]1[C:34]([O:35][CH3:36])=[CH:33][C:28]2[NH:29][C:30](=[O:32])[S:31][C:27]=2[CH:26]=1>>[CH2:22]([N:17]([CH2:18][CH2:19][O:20][CH3:21])[C:15]([CH:13]1[CH2:12][CH2:11][C:10]2[C:3]3[C:2]([NH:24][C:25]4[C:34]([O:35][CH3:36])=[CH:33][C:28]5[NH:29][C:30](=[O:32])[S:31][C:27]=5[CH:26]=4)=[N:7][CH:6]=[N:5][C:4]=3[S:8][C:9]=2[CH2:14]1)=[O:16])[CH3:23]

Participants

3

Reactant 2

HCID 900149486-amino-5-methoxy-1,3-benzothiazol-2(3H)-oneHCID 90014971(RS)-4-chloro-N-ethyl-N-(2-methoxyethyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxamide

Product 1

HCID 90014552(RS)-N-Ethyl-N-(2-methoxyethyl)-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 (283 μmol) (RS)-4-chloro-N-ethyl-N-(2-methoxyethyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxamide (prepared according to intermediate example 90a) 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 11.0 mg (7%) of the title compound.

Workup

  1. customto give
  2. custompurification 11.0 mg (7%) of the title compound

Sources & evidence

ORD record
ord-659d8dc623764b77a3b512c47f8f1d25
Source dataset
uspto-grants-2016_03
Patent number
US09296757B2

Reaction notes

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