Water → 4-{4-[4-(3-Methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid methyl ester

HRID 237421Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([NH2:12])[CH2:8][CH2:7]1)=[O:5])C.CCN(C(C)C)C(C)C.CS([C:25]1[N:30]=[C:29]([N:31]2[C:39]3[C:34](=[C:35]([O:40][CH2:41][CH2:42][CH2:43][S:44]([CH3:47])(=[O:46])=[O:45])[CH:36]=[CH:37][CH:38]=3)[CH:33]=[CH:32]2)[CH:28]=[CH:27][N:26]=1)=O.O>CC(N(C)C)=O>[CH3:1][O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:25]2[N:30]=[C:29]([N:31]3[C:39]4[C:34](=[C:35]([O:40][CH2:41][CH2:42][CH2:43][S:44]([CH3:47])(=[O:45])=[O:46])[CH:36]=[CH:37][CH:38]=4)[CH:33]=[CH:32]3)[CH:28]=[CH:27][N:26]=2)[CH2:8][CH2:7]1)=[O:5]

Participants

Conditions

Temperature: 120 °C

Procedure

4-Amino-cyclohexanecarboxylic acid ethyl ester (550 g) and 815 mL DIPEA were added to 1-(2-methanesulfinyl-pyrimidin-4-yl)-4-(3-methanesulfonyl-propoxy)-1H-indole (746.7 g) in 2.5 L DMA, and the mixture allowed to heat to 120° C. for 4 h and then allowed to cool to room temperature. Water (3 L) was added dropwise and the resulting precipitate was collected by filtration, washed with H2O and MeOH, and dried in vacuo at 48° C. overnight to yield 4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid methyl ester (90%).

Workup

temperatureto cool to room temperature
filtrationthe resulting precipitate was collected by filtration
washwashed with H2O and MeOH
customdried in vacuo at 48° C. overnight

Sources & evidence

ORD record: ord-756b6cb4452f420ab1aaddc184f78fbc
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642601B2

Reaction notes

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