3-[5-(2-Chloro-4-pyrimidinyl)-2-(1-methylethyl)-1,3-thiazol-4-yl]aniline → {3-[5-(2-Chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2,4-difluorophenyl}amine

HRID 1671130Notes

Reaction equation

HRID 1671130 reaction equation
ClC1N=C(C2SC(C(C)C)=NC=2C2C=C(C=CC=2)N)C=CN=1.[Cl:23][C:24]1[N:29]=[C:28]([C:30]2[S:34][C:33]([C:35]([CH3:38])([CH3:37])[CH3:36])=[N:32][C:31]=2[C:39]2[C:40]([F:53])=[C:41]([NH:46]C(=O)OCC=C)[CH:42]=[CH:43][C:44]=2[F:45])[CH:27]=[CH:26][N:25]=1>>[Cl:23][C:24]1[N:29]=[C:28]([C:30]2[S:34][C:33]([C:35]([CH3:38])([CH3:37])[CH3:36])=[N:32][C:31]=2[C:39]2[C:40]([F:53])=[C:41]([NH2:46])[CH:42]=[CH:43][C:44]=2[F:45])[CH:27]=[CH:26][N:25]=1

Participants

3

Reactant 2

HCID 579900463-[5-(2-Chloro-4-pyrimidinyl)-2-(1-methylethyl)-1,3-thiazol-4-yl]anilineHCID 57990078HCID 57990078, compound

Product 1

HCID 57989911{3-[5-(2-Chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2,4-difluorophenyl}amineYield 81%

Procedure

Following a procedure analogous to the procedure described in Intermediate 13 using 2-propen-1-yl {3-[5-(2-chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2,4-difluorophenyl}carbamate (2.962 g, 6.37 mmol) (from composite batches prepared as described above) the title compound of Step B was obtained (1.96 g, 81% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.67 (d, J=5.3 Hz, 1H), 7.09 (d, J=5.3 Hz, 1H), 6.88-7.02 (m, 2H), 5.23 (s, 2H), 1.45 (s, 9H); MS (ESI): 380 [M+H]+.

Sources & evidence

ORD record
ord-687ee76e48624d6da39bba8d39c6e660
Source dataset
uspto-grants-2011_08
Patent number
US07994185B2

Reaction notes

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