4-[4-(3-amino-2-fluorophenyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-5-yl]-2-pyrimidinamine → N-{3-[5-(2-amino-4-pyrimidinyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2-pyrazinesulfonamide

HRID 1962032Notes

Reaction equation

HRID 1962032 reaction equation
[NH2:1][C:2]1[C:3]([F:26])=[C:4]([C:8]2[N:9]=[C:10]([CH:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH2:19])[N:14]=2)[CH:5]=[CH:6][CH:7]=1.[N:27]1[CH:32]=[CH:31][N:30]=[CH:29][C:28]=1[S:33]([O-:35])=[O:34].[Na+]>>[NH2:19][C:15]1[N:14]=[C:13]([C:12]2[S:11][C:10]([CH:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)=[N:9][C:8]=2[C:4]2[C:3]([F:26])=[C:2]([NH:1][S:33]([C:28]3[CH:29]=[N:30][CH:31]=[CH:32][N:27]=3)(=[O:35])=[O:34])[CH:7]=[CH:6][CH:5]=2)[CH:18]=[CH:17][N:16]=1

Participants

3

Reactant 2

HCID 669150904-[4-(3-amino-2-fluorophenyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-5-yl]-2-pyrimidinamineHCID 66915242Sodium pyrazine-2-sulfinate

Product 1

HCID 57989967N-{3-[5-(2-amino-4-pyrimidinyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2-pyrazinesulfonamide

Procedure

Following a procedure analogous to the procedure described in Example 278 using 4-[4-(3-amino-2-fluorophenyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-5-yl]-2-pyrimidinamine (100 mg, 0.269 mmol) and sodium 2-pyrazinesulfinate (135 mg, 0.808 mmol), the title compound was obtained as a yellow solid (30 mg, 21% yield). MS (ESI): 514 [M−H]+.

Sources & evidence

ORD record
ord-21a51688e900401d9cc81fc68c3f2ab7
Source dataset
uspto-grants-2013_04
Patent number
US08415345B2

Reaction notes

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