N,N-Dimethylglycine hydrochloride → 2-(dimethylamino)-1-(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)ethanone

HRID 531790Notes

Reaction equation

HRID 531790 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.Cl.[CH3:81][N:82]([CH3:87])[CH2:83][C:84](O)=[O:85].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>[CH3:81][N:82]([CH3:87])[CH2:83][C:84]([N:29]1[CH2:30][CH2:31][N:26]([C:23]2[CH:24]=[CH:25][C:20]([C:17]3[CH:18]=[C:19]4[C:11]([C:9]5[CH:8]=[N:7][N:6]([CH2:5][C:4]6[CH:42]=[CH:43][CH:44]=[C:2]([F:1])[CH:3]=6)[CH:10]=5)=[CH:12][N:13]([S:32]([C:35]5[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=5)(=[O:34])=[O:33])[C:14]4=[N:15][CH:16]=3)=[CH:21][N:22]=2)[CH2:27][CH2:28]1)=[O:85]

Participants

8

Reactant 6

HCID 75605N,N-Dimethylglycine hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 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 1185240032-(dimethylamino)-1-(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)ethanone

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, 0.124 mmol) was coupled with 2-(dimethylamino)acetic acid hydrochloride (26 mg, 0.186 mmol) using HATU (71 mg, 0.186 mmol), HOBt (26 mg, 0.186 mmol) and DIPEA (87 μL, 0.498 mmol) in DMF (2 mL) to get 80 mg (93.0%) yield of the title compound. MS: m/z=693.3 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-4cd872bc9f274e5aa38131bf22504d15
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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