HCID 178448856, compound → HCID 178448855, compound

HRID 920661Notes

Reaction equation

HRID 920661 reaction equation
[CH2:1]([NH:5][C:6]1[N:7]=[CH:8][C:9]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[CH:13][N:12]([C@H:22]3[CH2:27][CH2:26][C@H:25]([O:28][Si](C(C)(C)C)(C)C)[CH2:24][CH2:23]3)[C:10]=2[N:11]=1)[CH2:2][CH2:3][CH3:4]>CO.Cl>[CH2:1]([NH:5][C:6]1[N:7]=[CH:8][C:9]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[CH:13][N:12]([C@H:22]3[CH2:23][CH2:24][C@H:25]([OH:28])[CH2:26][CH2:27]3)[C:10]=2[N:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 178448856HCID 178448856, compound

Product 1

HCID 178448855HCID 178448855, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

A solution of crude N-butyl-7-(trans-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)-5-(4-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine in MeOH (2.0 mL) was added a concentrated HCl solution (3 drops, 37% in water). The resulting solution was stirred at room temperature overnight, then concentrated. The residue was purified by pre-HPLC to provide the desired product (UNC1671A) (0.025 g, 36% over 3 steps). 1H NMR (400 MHz, CD3OD) δ 8.73 (s, 1H), 7.80 (s, 1H), 7.69-7.62 (m, 2H), 7.24-7.16 (m, 2H), 4.64-4.52 (m, 1H), 3.79-3.67 (m, 1H), 3.55 (t, J=7.1 Hz, 2H), 2.18-2.11 (m, 2H), 2.11-2.01 (m, 4H), 1.77-1.66 (m, 2H), 1.59-1.44 (m, 4H), 1.03 (t, J=7.4 Hz, 3H); MS m/z 383.2 [M+H]+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by pre-HPLC

Sources & evidence

ORD record
ord-5385644274484087abc0d4f37740e5d5
Source dataset
uspto-grants-2016_03
Patent number
US09273056B2

Reaction notes

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