Water → 3-Methoxymethyl-1-{2-[4-(4-pyrimidin-2-yl-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-acetyl}-pyrrolidine-3-carboxylic acid [3-(2-cyclopropyl-pyridin-4-yl)-1H-indazol-5-yl]-amide

HRID 1038057Notes

Reaction equation

HRID 1038057 reaction equation
[CH:1]1([C:4]2[CH:9]=[C:8]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20]([C:22]5([CH2:48][O:49][CH3:50])[CH2:26][CH2:25][N:24]([C:27](=[O:47])[CH2:28][N:29]6[CH2:34][CH:33]=[C:32]([C:35]7[CH:40]=[CH:39][C:38]([C:41]8[N:46]=[CH:45][CH:44]=[CH:43][N:42]=8)=[CH:37][CH:36]=7)[CH2:31][CH2:30]6)[CH2:23]5)=[O:21])[CH:17]=4)[N:12](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:11]=3)[CH:7]=[CH:6][N:5]=2)[CH2:3][CH2:2]1.ClCCl.O>FC(F)(F)C(O)=O>[CH:1]1([C:4]2[CH:9]=[C:8]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20]([C:22]5([CH2:48][O:49][CH3:50])[CH2:26][CH2:25][N:24]([C:27](=[O:47])[CH2:28][N:29]6[CH2:30][CH:31]=[C:32]([C:35]7[CH:36]=[CH:37][C:38]([C:41]8[N:42]=[CH:43][CH:44]=[CH:45][N:46]=8)=[CH:39][CH:40]=7)[CH2:33][CH2:34]6)[CH2:23]5)=[O:21])[CH:17]=4)[NH:12][N:11]=3)[CH:7]=[CH:6][N:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 6344DichloromethaneHCID 765923933-Methoxymethyl-1-{2-[4-(4-pyrimidin-2-yl-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-acetyl}-pyrrolidine-3-carboxylic acid [3-(2-cyclopropyl-pyridin-4-yl)-1-trityl-1H-indazol-5-yl]-amide

Product 1

HCID 674194913-Methoxymethyl-1-{2-[4-(4-pyrimidin-2-yl-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-acetyl}-pyrrolidine-3-carboxylic acid [3-(2-cyclopropyl-pyridin-4-yl)-1H-indazol-5-yl]-amideYield 105.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

3-Methoxymethyl-1-{2-[4-(4-pyrimidin-2-yl-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-acetyl}-pyrrolidine-3-carboxylic acid [3-(2-cyclopropyl-pyridin-4-yl)-1-trityl-1H-indazol-5-yl]-amide (570 mg, 0.63 mmol) was dissolved in 4 ml of trifluoroacetic acid (TFA), 10 ml dichloromethane and 2 ml of water and the reaction mixture was stirred for 18 hrs. The reaction mixture was evaporated and chromatographed on silica gel using 3-5% 2N NH3/methanol/dichlormethane to obtain 444 mg of title product. MS (M+1)=669. Retention time (minutes) 2.67.

Workup

  1. customThe reaction mixture was evaporated
  2. customchromatographed on silica gel using 3-5% 2N NH3/methanol/dichlormethane

Sources & evidence

ORD record
ord-482e38d76baf4d65b3342ed8617fb79d
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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