1-Hydroxybenzotriazole → HCID 90031702, compound

HRID 531817Notes

Reaction equation

HRID 531817 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:42]=[CH:43][CH:44]=1)[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:21]=[N:22][C:23]([N:26]5[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]5)=[CH:24][CH:25]=4)[CH:18]=3)[N:13]([S:32]([C:35]3[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[CH:12]=2)[CH:8]=[N:7]1.FC1C=C(C=CC=1)CN1C=C(C2C3C(=NC=C(C4C=NC(N5CCN(C)CC5)=CC=4)C=3)NC=2)C=N1.[CH:80]1([CH2:83][C:84](O)=[O:85])[CH2:82][CH2:81]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:80]1([CH2:83][C:84]([N:29]2[CH2:30][CH2:31][N:26]([C:23]3[CH:24]=[CH:25][C:20]([C:17]4[CH:18]=[C:19]5[C:11]([C:9]6[CH:8]=[N:7][N:6]([CH2:5][C:4]7[CH:42]=[CH:43][CH:44]=[C:2]([F:1])[CH:3]=7)[CH:10]=6)=[CH:12][N:13]([S:32]([C:35]6[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=6)(=[O:34])=[O:33])[C:14]5=[N:15][CH:16]=4)=[CH:21][N:22]=3)[CH2:27][CH2:28]2)=[O:85])[CH2:82][CH2:81]1

Participants

8

Reactant 6

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 138440Cyclopropaneacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 900303003-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 900309313-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 90031702HCID 90031702, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-124, 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (step 1 compound of example 137) (75 mg, 0.123 mmol) was coupled with 2-cyclopropylacetic acid (19 mg, 0.185 mmol) using HATU (70 mg, 0.185 mmol), HOBt (25 mg, 0.185 mmol) and DIPEA (48 mg, 0.37 mmol) in DMF (3 mL) to get 80 mg (95.2.0%) yield of the title compound. MS: m/z=690.6 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-a359c256ac934a67885ff251584e4af5
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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