Triethylamine → HCID 46917569, compound

HRID 1256454Notes

Reaction equation

[F:1][CH:2]([F:34])[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]([CH3:21])[CH:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[CH:11]=[C:10]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[N:9]=2)[C:6]2[CH:28]=[CH:29][CH:30]=[C:31]([O:32][CH3:33])[C:5]=2[N:4]=1.CCN(CC)CC.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>C1COCC1.O>[F:34][CH:2]([F:1])[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]([CH3:21])[CH:15]3[CH2:20][CH2:19][N:18]([S:43]([CH3:42])(=[O:45])=[O:44])[CH2:17][CH2:16]3)[CH:11]=[C:10]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[N:9]=2)[C:6]2[CH:28]=[CH:29][CH:30]=[C:31]([O:32][CH3:33])[C:5]=2[N:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 95 mg (2 mmol) of 2-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-methyl-6-(4-morpholinyl)-N-(4-piperidinyl)-4-pyrimidinamine and 61 mg (6 mmol) of Et3N in 15 mL THF was cooled to 0° C. and 46 mg (4 mmol) of methanesulphonyl chloride was added. The stirred mixture was allowed to warm to room temperature, and after 2 hrs it was diluted with water to give a precipitate of 98 mg (89% yield) of 2-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-methyl-N-[1-(methylsulfonyl)-4-piperidinyl]-6-(4-morpholinyl)-4-pyrimidinamine: mp (MeOH) 191-193° C.; 1H NMR (CDCl3) δ 7.77 (dd, J=8.4. 0.6 Hz, 1H), 7.37 (t, JHF=53.4 Hz, 1H), 7.31 (t, J=8.2 Hz, 1H), 6.79 (d, J=7.6 Hz, 1H), 5.40 (s, 1H), 4.96 (m, 1H), 4.05 (s, 3H), 3.99-3.93 (m, 2H), 3.83 (m, 4H), 3.64 (m, 4H), 2.90 (s, 3H), 2.82 (s, 3H), 2.81 (dt, J=12.0, 2.4 Hz, 2H), 1.91 (dq J=12.3, 4.3 Hz, 2H), 1.85-1.76 (m, 2H); Anal. Calcd. for C24H31F2N7O4S: C, 52.3; H, 5.7; N, 17.8. Found: C, 52.5; H, 5.7; N, 17.9%.

Workup

temperatureto warm to room temperature

Sources & evidence

ORD record: ord-d2e766bc4b974edc88d834061ce2b76c
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461158B2

Reaction notes

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