Ethyl 4-chloro-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine-7-carboxylate → (RS)-Ethyl 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-carboxylate

HRID 930975Notes

Reaction equation

HRID 930975 reaction equation
Cl[C:2]1[C:3]2[C:10]3[CH2:11][CH2:12][CH:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:14][C:9]=3[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:20][C:21]1[C:30]([O:31][CH3:32])=[CH:29][C:24]2[NH:25][C:26](=[O:28])[S:27][C:23]=2[CH:22]=1>>[CH3:32][O:31][C:30]1[C:21]([NH:20][C:2]2[C:3]3[C:10]4[CH2:11][CH2:12][CH:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:14][C:9]=4[S:8][C:4]=3[N:5]=[CH:6][N:7]=2)=[CH:22][C:23]2[S:27][C:26](=[O:28])[NH:25][C:24]=2[CH:29]=1

Participants

3

Reactant 2

HCID 17990004Ethyl 4-chloro-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine-7-carboxylateHCID 900149486-amino-5-methoxy-1,3-benzothiazol-2(3H)-one

Product 1

HCID 118119941(RS)-Ethyl 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-carboxylate

Procedure

130 mg (438 μmol) (RS)-ethyl 4-chloro-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxylate (prepared according to intermediate example 1a) 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 98.1 mg (47%) of the title compound.

Workup

  1. customto give
  2. custompurification 98.1 mg (47%) of the title compound

Sources & evidence

ORD record
ord-2bfd57e2c2514feb9ace8c13eb9b673b
Source dataset
uspto-grants-2016_03
Patent number
US09296757B2

Reaction notes

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