Formaldehyde → HCID 86292429, compound

HRID 1521955Notes

Reaction equation

HRID 1521955 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[NH:29][C:10]3=[N:11][CH:12]=[CH:13][C:14]([C:15]4[N:20]=[C:19]([NH:21][CH2:22][CH:23]5[CH2:28][CH2:27][O:26][CH2:25][CH2:24]5)[CH:18]=[CH:17][CH:16]=4)=[C:9]3[CH:8]=2)[CH2:3][CH2:2]1.C=O.O.[C:33]([BH3-])#N.[Na+]>CO.ClCCl>[CH3:33][N:1]1[CH2:6][CH2:5][CH:4]([C:7]2[NH:29][C:10]3=[N:11][CH:12]=[CH:13][C:14]([C:15]4[N:20]=[C:19]([NH:21][CH2:22][CH:23]5[CH2:28][CH2:27][O:26][CH2:25][CH2:24]5)[CH:18]=[CH:17][CH:16]=4)=[C:9]3[CH:8]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 86292428HCID 86292428, compound

Product 1

HCID 86292429HCID 86292429, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of Example 88C (15 mg, 0.04 mmol) in methanol (2 mL) was treated with 37% formaldehyde in water (12 mg, 0.4 mmol) and the mixture was stirred at room temperature for 1 hour. Sodium cyanoborohydride (5 mg, 0.08 mmol) was added and the mixture was stirred at room temperature for 12 hours. The mixture was diluted with dichloromethane and washed with water. The organic phase was concentrated and purified by HPLC (Zorbax C-18, using a 0-100% gradient of water/acetonitrile, containing 0.1% trifluoroacetic acid) to afford the title compound. 1H NMR (400 MHz, DMSO-d6): δ 1.17-1.38 (m, 2H), 1.64-1.73 (m, 2H), 1.77-1.96 (m, 4H), 2.34 (d, J=13.56 Hz, 4H), 2.83 (d, J=4.75 Hz, 3H), 3.00-3.20 (m, 4H), 3.56 (d, J=11.53 Hz, 2H), 3.88 (dd, J=10.68, 3.22 Hz, 2H), 6.68 (d, J=8.48 Hz, 1H), 6.77-6.83 (m, 1H), 7.18 (d, J=7.80 Hz, 1H), 7.50 (d, J=5.09 Hz, 1H), 7.58-7.63 (m, 1H), 8.24-8.27 (m, 1H). LCMS: 406 (M+H)+.

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. washwashed with water
  3. concentrationThe organic phase was concentrated
  4. custompurified by HPLC (Zorbax C-18
  5. additioncontaining 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-eee8dcaed98840daaa5ee710f290dde6
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

Loading…