Acetic Acid → HCID 66980218, compound

HRID 1423316Notes

Reaction equation

HRID 1423316 reaction equation
[NH2:1][C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]3[CH:12]=[N:13][C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:15][CH:16]=3)=[C:6]2[N:5]=[C:4]2[C:23](=O)[CH2:24][CH2:25][C:3]=12.[O:27]1[CH2:32][CH2:31][CH:30]([NH2:33])[CH2:29][CH2:28]1.CC(O)=O.[BH3-]C#N.[Na+]>CCO>[C:17]1([C:14]2[N:13]=[CH:12][C:11]([C:10]3[CH:9]=[N:8][N:7]4[C:2]([NH2:1])=[C:3]5[CH2:25][CH2:24][CH:23]([NH:33][CH:30]6[CH2:31][CH2:32][O:27][CH2:28][CH2:29]6)[C:4]5=[N:5][C:6]=34)=[CH:16][CH:15]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 4192234-AminotetrahydropyranHCID 5003444Sodium cyanoborohydrideHCID 66980245HCID 66980245, compound

Product 1

HCID 66980218HCID 66980218, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 8-amino-3-(6-phenylpyridin-3-yl)-6,7-dihydro-5H-cyclopenta[d]pyrazolo[1,5-a]pyrimidin-5-one (61.5 mg, 0.18 mmol), tetrahydro-2H-pyran-4-amine (100 uL), HOAc (100 uL) in EtOH (2 mL) was stirred at room temperature for 15 min. NaBH3CN (56.7 mg, 0.90 mmol) was added and the reaction was stirred overnight. Purification with prep-LC provided 3-(6-phenylpyridin-3-yl)-N5-(tetrahydro-2H-pyran-4-yl)-6,7-dihydro-5H-cyclopenta[d]pyrazolo[1,5-a]pyrimidine-5,8-diamine: LCMS tR=2.35 Min (10 min run, UV254nm), Mass calculated for, M+426.0, observed LC/MS m/z 427.0 (M+H).

Workup

  1. stirringthe reaction was stirred overnight
  2. customPurification

Sources & evidence

ORD record
ord-f139b81b07684262b3dcf2f13261d81e
Source dataset
uspto-grants-2015_01
Patent number
US08927562B2

Reaction notes

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