Methanol → HCID 21923079, compound

HRID 1244941Notes

Reaction equation

HRID 1244941 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[N:13]=[C:12]([Cl:14])[N:11]=[C:10]2[C:6]=1[N:7]=[CH:8][N:9]2[CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.CO.[F:22][C:23]([F:34])([F:33])[O:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1.[BH3-]C#N.[Na+]>C(O)(=O)C>[Cl:14][C:12]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:5]([NH:4][CH2:3][CH2:2][NH:1][CH2:29][C:28]2[CH:31]=[CH:32][C:25]([O:24][C:23]([F:22])([F:33])[F:34])=[CH:26][CH:27]=2)[N:13]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 69573p-(Trifluoromethoxy)benzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21922924N-(2-aminoethyl)-2-chloro-9-cyclopentyl-9H-purin-6-amine

Product 1

HCID 21923079HCID 21923079, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

281 mg of the product obtained in Stage 1 of Example 7, 4 ml of methanol, 0.16 ml of 4-trifluoromethoxy-benzaldehyde and 0.2 ml of acetic acid are mixed together, the reaction medium is agitated for 2 hours and 30 minutes, 0.1 g of NaBH3CN is added and agitation is carried out at ambient temperature for 1 hour. The solvent is evaporated off, the residue is chromatographed on silica eluting with CH2Cl2/methanol/ammonium hydroxide (95/0.5/0.33) and 129 mg of expected product is obtained.

Workup

  1. waitagitation is carried out at ambient temperature for 1 hour
  2. customThe solvent is evaporated off
  3. customthe residue is chromatographed on silica eluting with CH2Cl2/methanol/ammonium hydroxide (95/0.5/0.33)

Sources & evidence

ORD record
ord-758a53d2f2ab488ba3fa2e49e079228c
Source dataset
uspto-grants-2006_10
Patent number
US07122669B1

Reaction notes

Loading…