Potassium Phosphate, Tribasic → HCID 68865649, compound

HRID 1726009Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[CH2:18][CH2:17][CH2:16][CH:15](C)[C:14]=2[C:13]=1[C:23]([O:25]C)=[O:24])(=[O:10])=[O:9].[F:27][C:28]([F:46])([F:45])[C:29]1[CH:34]=[CH:33][N:32]=[C:31]([N:35]2[CH2:40][CH2:39][N:38]([CH2:41][CH2:42][CH2:43][NH2:44])[CH2:37][CH2:36]2)[N:30]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN1CCCC1=O>[F:46][C:28]([F:27])([F:45])[C:29]1[CH:34]=[CH:33][N:32]=[C:31]([N:35]2[CH2:40][CH2:39][N:38]([CH2:41][CH2:42][CH2:43][NH:44][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[S:8]([NH:11][C:12]3[CH:21]=[CH:20][C:19]4[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=4[C:13]=3[C:23]([OH:25])=[O:24])(=[O:9])=[O:10])[CH2:37][CH2:36]2)[N:30]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of Example 275F (100 mg, 0.275 mmol) in 1.0 mL of N-methylpyrrolidinone was treated with 151 mg of 3-[4-(4-trifluoromethylpyrimidin-2-yl)-piperazin-1-yl]-propylamine and 58 mg of potassium phosphate, warmed to 160° C., stirred for 16 hours, concentrated, and purified by C18 reverse-phase HPLC using acetonitrile/water/0.1% TFA to provide the desired product (63 mg, 36%). MS (ESI) m/e 619 (M+H)+; 1H NMR (400 MHz, CD3OD) δ 8.66 (d, J=4.80 Hz, 1H), 7.52 (dd, J=7.96, 1.51 Hz, 1H), 7.34 (m, 1H), 7.24 (d, J=8.37 Hz, 1H), 7.03 (d, J=4.94 Hz, 1H), 6.97 (d, J=8.37 Hz, 1H), 6.80 (d, J=7.68 Hz, 1H), 6.57-6.61 (m, 1H), 3.75-4.25 (m, 4H), 3.25-3.40 (m, 8H), 2.65-2.76 (m, 4H), 2.03-2.10 (m, 2H), 1.65-1.69 (m, 4H).

Workup

concentrationconcentrated
custompurified by C18 reverse-phase

Sources & evidence

ORD record: ord-c2c96ccd594a42bf85b2c06a6fb641b2
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491718B2

Reaction notes

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