Hydrochloric Acid → HCID 67812950, compound

HRID 2284546Notes

Reaction equation

HRID 2284546 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([NH:14][CH2:15][CH2:16][CH2:17][N:18]([CH2:20][C@@H:21]2[C@@H:25]([OH:26])[C@@H:24]([OH:27])[C@H:23]([N:28]3[C:32]4[N:33]=[CH:34][N:35]=[C:36]([NH:37][CH2:38][C:39]5[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][C:40]=5[O:47][CH3:48])[C:31]=4[CH:30]=[CH:29]3)[O:22]2)[CH3:19])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[ClH:49].O>CO>[ClH:49].[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([NH:14][CH2:15][CH2:16][CH2:17][N:18]([CH2:20][C@@H:21]2[C@@H:25]([OH:26])[C@@H:24]([OH:27])[C@H:23]([N:28]3[C:32]4[N:33]=[CH:34][N:35]=[C:36]([NH:37][CH2:38][C:39]5[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][C:40]=5[O:47][CH3:48])[C:31]=4[CH:30]=[CH:29]3)[O:22]2)[CH3:19])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 67811659HCID 67811659, compound

Product 1

HCID 67812950HCID 67812950, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(4-(tert-butyl)phenyl)-3-(3-((((2R,3S,4R,5R)-5-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)(methyl)amino)propyl)urea (20 mg, 0.039 mmol) in methanol (0.7 mL) was added to a mixture of 0.1N HCl (0.39 mL, 0.039 mmol) and water (2.0 mL). The colorless solution was concentrated in vacuo to remove the methanol. The solution was lyophilized to yield the title compound (20 mg, 93%) as a white solid: 1H NMR (400 MHz, D2O) ppm 8.02 (s, 1H), 7.33 (d, J=3.73 Hz, 1H), 7.21 (d, J=8.09 Hz, 2H), 6.90 (d, J=8.09 Hz, 2H), 6.69 (d, J=3.73 Hz, 1H), 6.13 (d, J=4.56 Hz, 1H), 4.47 (m, 2H), 4.24 (t, J=5.39 Hz, 1H), 3.67 (m, 1H), 3.54 (d, J=12.02 Hz, 1H), 3.33 (m, 1H), 3.22 (m, 1H), 3.11 (m, 1H), 2.94 (s, 3H), 1.90 (m, 2H), 1.20 (s, 9H); MS (ESI+) for C26H37N7O4 m/z 512.3 (M+H)+; (ESI−) for C26H37N7O4 m/z 510.2 (M−H)−; HPLC purity 97% (ret. time, 2.82 min). IC50<10 nM.

Workup

  1. concentrationThe colorless solution was concentrated in vacuo
  2. customto remove the methanol

Sources & evidence

ORD record
ord-00d14a23392647839b3f0b1fb568b26f
Source dataset
uspto-grants-2015_09
Patent number
US09145438B2

Reaction notes

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