Dichloromethane → HCID 70168839, compound

HRID 1426944Notes

Reaction equation

HRID 1426944 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C.C(Cl)Cl.[NH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=1[C@H:33]1[CH2:37][CH2:36][CH2:35][N:34]1[C:38]1[CH:43]=[CH:42][N:41]2[N:44]=[CH:45][C:46]([CH:47]=O)=[C:40]2[N:39]=1>[Cl-].[Na+].O>[F:32][C:29]1[CH:28]=[C:27]2[C:26](=[CH:31][CH:30]=1)[O:25][CH2:24][CH2:23][NH:22][CH2:47][C:46]1=[C:40]3[N:39]=[C:38]([CH:43]=[CH:42][N:41]3[N:44]=[CH:45]1)[N:34]1[C@@H:33]2[CH2:37][CH2:36][CH2:35]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)HCID 86691735HCID 86691735, compound

Product 1

HCID 70168839HCID 70168839, compoundYield 21.6%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

Tetramethylammonium triacetoxyborohydride (46.7 mg, 0.629 mmol) was added to a DCM (50 mL) solution of (R)-5-(2-(2-(2-aminoethoxy)-5-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (155 mg, 0.420 mmol), and the reaction was stirred at ambient temperature overnight. The reaction mixture was then diluted with brine and extracted with several portions of DCM in a phase separator tube, and the combined organic extracts were concentrated and purified by reverse-phase column chromatography, eluting with 0-90% acetonitrile-H2O, to obtain the title product (32 mg, 21.6% yield). MS (apci) m/z=354.2 (M+H).

Workup

  1. extractionextracted with several portions of DCM in a phase separator tube
  2. concentrationthe combined organic extracts were concentrated
  3. custompurified by reverse-phase column chromatography
  4. washeluting with 0-90% acetonitrile-H2O

Sources & evidence

ORD record
ord-f48b8039b96c4ab492957055824dbc35
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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