Water → HCID 66897134, compound

HRID 1969490Notes

Reaction equation

HRID 1969490 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[N:12][N:13]([CH2:15][C:16](OC)=[O:17])[CH:14]=2)[C:5]([C:20]#[N:21])=[C:4]([S:22][CH2:23][C:24]2[N:25]=[C:26]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[S:27][CH:28]=2)[N:3]=1.[BH4-].[Na+].O>CO.C1COCC1>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[N:12][N:13]([CH2:15][CH2:16][OH:17])[CH:14]=2)[C:5]([C:20]#[N:21])=[C:4]([S:22][CH2:23][C:24]2[N:25]=[C:26]([C:29]3[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=3)[S:27][CH:28]=2)[N:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydride2×HCID 70252855HCID 70252855, compound

Product 1

HCID 66897134HCID 66897134, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

80 mg (0.153 mmol) of the compound from Example 19A were initially charged in 3 ml of methanol and 3 ml of THF, and 17 mg (0.460 mmol) of sodium borohydride were added. The reaction mixture was stirred at RT for 1 h, another 17 mg (0.460 mmol) of sodium borohydride were then added and the mixture was stirred at RT for 1 h. A little water was added to the reaction, and the product was purified directly by preparative HPLC (acetonitrile/water 10:90→95:5, 0.1% TFA added).

Workup

  1. stirringthe mixture was stirred at RT for 1 h
  2. customthe product was purified directly by preparative HPLC (acetonitrile/water 10:90→95:5, 0.1% TFA added)

Sources & evidence

ORD record
ord-005546e124f8451ebe3787868e271a9d
Source dataset
uspto-grants-2013_04
Patent number
US08426602B2

Reaction notes

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