Diisopropylethylamine → HCID 136983681, compound

HRID 64379Notes

Reaction equation

HRID 64379 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:28]([C:29]([NH2:31])=[O:30])=[C:17]3[NH:18][CH2:19][CH2:20][C@@H:21]([CH:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)[N:16]3[N:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:32]([O:36][C:37]([NH:39][CH2:40][CH2:41][N:42]1[CH2:47][CH2:46][N:45]([CH2:48]/[CH:49]=[CH:50]/[C:51](O)=[O:52])[CH2:44][CH2:43]1)=[O:38])([CH3:35])([CH3:34])[CH3:33].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[C:29]([C:28]1[C:14]([C:11]2[CH:10]=[CH:9][C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:13][CH:12]=2)=[N:15][N:16]2[C@H:21]([CH:22]3[CH2:23][CH2:24][N:25]([C:51](=[O:52])/[CH:50]=[CH:49]/[CH2:48][N:45]4[CH2:46][CH2:47][N:42]([CH2:41][CH2:40][NH:39][C:37](=[O:38])[O:36][C:32]([CH3:33])([CH3:35])[CH3:34])[CH2:43][CH2:44]4)[CH2:26][CH2:27]3)[CH2:20][CH2:19][NH:18][C:17]=12)(=[O:30])[NH2:31]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59799013HCID 59799013, compoundHCID 136928097Pyrazolo[1,5-a]pyrimidine-3-carboxamide, 4,5,6,7-tetrahydro-2-(4-phenoxyphenyl)-7-(4-piperidinyl)-, (7S)-

Product 1

HCID 136983681HCID 136983681, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of (S)-2-(4-phenoxyphenyl)-7-(piperidin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide (1.26 g, 3.03 mmol), (E)-4-(4-(2-((tert-butoxycarbonyl)amino)ethyl)piperazin-1-yl)but-2-enoic acid (948.4 mg, 3.03 mmol), HATU (1.21 g, 3.18 mmol), DIEA (782 mg, 6.06 mmol) in 30 mL of DMF was stirred at RT for 15 hr. The mixture was poured into 300 mL of water and extracted with EA (100 mL). The organic phase was washed with water (100 mL×3) and concentrated to give 1.25 g (58%) of product as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 7.50 (d, J=8.4 Hz, 2H), 7.42 (t, J=8.4 Hz, 2H), 7.17 (t, J=7.4 Hz, 1H), 7.12-7.02 (m, 4H), 6.67 (br s, 1H), 6.64-6.53 (m, 3H), 4.53-4.40 (m, 1H), 4.14-4.05 (m, 1H), 3.32-3.25 (m, 2H), 3.10-2.91 (m, 5H), 2.45-2.15 (m, 1H), 2.10-2.00 (m, 1H), 1.96-1.84 (m, 1H), 1.78-1.65 (m, 1H), 1.62-1.50 (m, 1H), 1.37 (s, 9H), 1.31-1.10 (m, 3H). MS (ESI) m/e [M+1]+713.0.

Workup

  1. extractionextracted with EA (100 mL)
  2. washThe organic phase was washed with water (100 mL×3)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ed12894827794d7c932928b4cc46438b
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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