Cyclopropanol → (R)-4-{1-[6-(4-Fluoro-phenyl)-4-cyclopropoxy-pyrido[3,2-d]pyrimidin-2-ylamino]-ethyl}-benzenesulfonamide

HRID 42351Notes

Reaction equation

HRID 42351 reaction equation
N1([O:10][C:11]2[C:12]3[N:33]=[C:32]([C:34]4[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=4)[CH:31]=[CH:30][C:13]=3[N:14]=[C:15]([NH:17][C@@H:18]([C:20]3[CH:25]=[CH:24][C:23]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:22][CH:21]=3)[CH3:19])[N:16]=2)C2C=CC=CC=2N=N1.[CH:41]1(O)[CH2:43][CH2:42]1>COCCOC>[F:40][C:37]1[CH:38]=[CH:39][C:34]([C:32]2[CH:31]=[CH:30][C:13]3[N:14]=[C:15]([NH:17][C@@H:18]([C:20]4[CH:21]=[CH:22][C:23]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:24][CH:25]=4)[CH3:19])[N:16]=[C:11]([O:10][CH:41]4[CH2:43][CH2:42]4)[C:12]=3[N:33]=2)=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 123361CyclopropanolHCID 58275536HCID 58275536, compound

Product 1

HCID 58275547(R)-4-{1-[6-(4-Fluoro-phenyl)-4-cyclopropoxy-pyrido[3,2-d]pyrimidin-2-ylamino]-ethyl}-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of (R)-4-(1-(4-(1H-benzo[d][1, 2, 3]triazol-1-yloxy)-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidin-2-ylamino)ethyl)benzenesulfonamide (80 mg), cyclopropanol (0.1 ml) and CsCO3 (94 mg) in DME (3 ml) was stirred at room temperature over the weekend. The reaction mixture was concentrated and purified by reverse phase HPLC (eluting with ACN/H2O+0.1% TFA) to give the title compound, which was characterized by its NMR and mass spectrum as follows: 1H NMR (CD3OD): d 0.83-1.04 (m, 4H), 1.66-1.70 (m, 3H). 4.50-4.58 (m, 1H), 5.40-5.49 (m, 1H), 7.19 (t, 2H), 7.61-7.88 (m, 4H), 7.99-8.02 (m, 1H), 8.08-8.13 (m, 2H), 8.30 (s, 1H); MS (m/z): 480.3 ([M+H]+, 100).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by reverse phase HPLC (eluting with ACN/H2O+0.1% TFA)

Sources & evidence

ORD record
ord-2f3fb4c6a1004f0f8735458e7919160f
Source dataset
uspto-grants-2013_09
Patent number
US08536187B2

Reaction notes

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