Acetic Acid → HCID 86653762, compound

HRID 2189112Notes

Reaction equation

HRID 2189112 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:16]([NH:18][C@H:19]4[CH2:24][CH2:23][CH2:22][C@H:21]([NH2:25])[CH2:20]4)=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:5][CH:4]=1.C(O)(=O)C.[CH3:36][O:37][C:38](=[O:41])[CH:39]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.O>[CH3:36][O:37][C:38](=[O:41])[CH2:39][NH:25][C@H:21]1[CH2:22][CH2:23][CH2:24][C@H:19]([NH:18][C:16]2[C:17]3[C:9]([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)=[C:10]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[O:11][C:12]=3[N:13]=[CH:14][N:15]=2)[CH2:20]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 70205Acetic acid, 2-oxo-, methyl esterHCID 5049666Sodium triacetoxyborohydrideHCID 86653763HCID 86653763, compound

Product 1

HCID 86653762HCID 86653762, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 132 mg (0.318 mmol) of −(+/−)-cis/trans-N-[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]-cyclohexane-1,3-diamine (Example 36A) in 1.5 ml of dichloromethane and add 18.7 μl of acetic acid at RT. Add 28 mg (0.318 mmol) of oxoacetic acid methyl ester and, after 5 min, 101 mg (0.478 mmol) of sodium triacetoxyborohydride. Stir the mixture at RT for 2 h and then dilute with water and dichloromethane. Wash the organic phase with saturated sodium carbonate solution, dry over sodium sulphate and concentrate under reduced pressure. Purify the crude product by preparative RP-HPLC (eluent: acetonitrile/water gradient) and separate the cis/trans isomers:

Workup

  1. washWash the organic phase with saturated sodium carbonate solution
  2. dry with materialdry over sodium sulphate
  3. concentrationconcentrate under reduced pressure
  4. customPurify the crude product by preparative RP-HPLC (eluent: acetonitrile/water gradient)
  5. customseparate the cis/trans isomers

Sources & evidence

ORD record
ord-c2fe2bf9f160467e9ff2777dc80f1c41
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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