Formaldehyde → HCID 25160324, compound

HRID 914016Notes

Reaction equation

HRID 914016 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:14][O:15][CH:16]([C:18]3[CH:19]=[C:20]([N:27]([CH3:29])[CH3:28])[CH:21]=[C:22]4[C:26]=3[NH:25][N:24]=[CH:23]4)[CH3:17])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:30]([BH3-])#N.[Na+].C=O>C(#N)C.C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:14][O:15][CH:16]([C:18]3[CH:19]=[C:20]([N:27]([CH3:28])[CH3:29])[CH:21]=[C:22]4[C:26]=3[NH:25][N:24]=[CH:23]4)[CH3:17])[CH2:13][CH2:12][N:11]([CH3:30])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 57546093HCID 57546093, compound

Product 1

HCID 25160324HCID 25160324, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6342AcetonitrileSolvent

Procedure

To a suspension of (±)-7-(1-((4-(4-fluorophenyl)piperidin-4-yl)methoxy)ethyl)-N,N-dimethyl-1H-indazol-5-amine (101 mg, 0.255 mmol) and sodium cyanoborohydride (80 mg, 1.27 mmol) in acetonitrile (6 mL) at 0° C. was added formalin (0.053 mL). The reaction was treated with 5 drops of acetic acid and the ice bath was removed, stirring continued for 2 h. The reaction was concentrated and purified by preparative HPLC to give 78.5 mg (75%). 1H-NMR (CDCl3, 500 MHz) δ 8.17 (s, 1H), 7.90 (s, 1H), 7.38 (s, 1H), 7.23 (m, 3H), 7.10 (m, 2H), 4.66 (q, J=5.0 Hz, 1H), 3.50-3.57 (m, 2H), 3.39 (d, J=10 Hz, 1H), 3.27 (s, 6H), 3.18 (d, J=10 Hz, 1H), 2.74 (s, 3H), 2.50-2.73 (m, 4H), 2.35-2.45 (m,2H), 1.51 (d, J=5.0 Hz, 3H); Mass spec.: 411.45 (MH)+.

Workup

  1. customthe ice bath was removed
  2. concentrationThe reaction was concentrated
  3. custompurified by preparative HPLC
  4. customto give 78.5 mg (75%)

Sources & evidence

ORD record
ord-03d052ed979e4f2ea29f1bea491c706c
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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