Hydrochloric Acid → HCID 67811385, compound

HRID 1024666Notes

Reaction equation

HRID 1024666 reaction equation
[NH2:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:15][C@H:14]([CH2:16][N:17]([CH:35]([CH3:37])[CH3:36])[CH2:18][CH2:19][CH2:20][NH:21][C:22]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:27][CH:26]=4)=[O:23])[C@@H:13]([OH:38])[C@H:12]3[OH:39])[C:4]=2[N:5]=[CH:6][N:7]=1.[ClH:40].O>CO>[ClH:40].[NH2:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:15][C@H:14]([CH2:16][N:17]([CH:35]([CH3:36])[CH3:37])[CH2:18][CH2:19][CH2:20][NH:21][C:22]([NH:24][C:25]4[CH:26]=[CH:27][C:28]([C:31]([CH3:33])([CH3:32])[CH3:34])=[CH:29][CH:30]=4)=[O:23])[C@@H:13]([OH:38])[C@H:12]3[OH:39])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 569623361-[3-[[(2R,3S,4R,5R)-5-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-3,4-dihydroxyoxolan-2-yl]methyl-propan-2-ylamino]propyl]-3-(4-tert-butylphenyl)urea

Product 1

HCID 67811385HCID 67811385, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(3-((((2R,3S,4R,5R)-5-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)(isopropyl)amino)propyl)-3-(4-(tert-butyl)phenyl)urea (1.64 g, 3.04 mmol) in 50 mL 50% aq methanol was treated with 1.0N of hydrogen chloride in water (3.87 mL, 3.04 mmol). The solution was concentrated to remove most of the methanol and lyophilized overnight. The cloudy mixture was filtered through a fine frit and the filtrate was concentrated in vacuo to remove the MeOH. The resultant solution was lyophilized overnight to yield the title compound (1.70 g, 97%) as a solid: MS (ESI+) for C28H41N7O4 m/z 540.4 (M+H)+; MS (ESI+) for C28H41N7O4 m/z 538.4 (M+H)+, m/z 574.4 (M+Cl)−; HPLC purity 97% (ret. time, 2.88 min); 1H NMR (400 MHz, d4-MeOH) ppm 8.12 (s, 1H), 7.29 (m, 2H), 7.23 (m, 3H), 6.68 (m, 1H), 6.09 (br. s., 1H), 4.57 (m, 1H), 4.35 (m, 2H), 3.79 (br. s., 1H), 3.55 (m, 2H), 3.26 (br. s., 4H), 1.94 (m, 2H), 1.35 (m, 6H), 1.29 (s, 9H). IC50<10 nM.

Workup

  1. concentrationThe solution was concentrated
  2. customto remove most of the methanol
  3. filtrationThe cloudy mixture was filtered through a fine frit
  4. concentrationthe filtrate was concentrated in vacuo
  5. customto remove the MeOH
  6. waitThe resultant solution was lyophilized overnight

Sources & evidence

ORD record
ord-a2154d475c494452917856712e67cb25
Source dataset
uspto-grants-2014_05
Patent number
US08722877B2

Reaction notes

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