Sodium cyanoborohydride → HCID 86702116, compound

HRID 873603Notes

Reaction equation

HRID 873603 reaction equation
[CH3:1][C:2]1([CH2:8][N:9]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]([CH:23]4[CH2:26][N:25]([C:27]5[N:28]=[N:29][C:30]([CH3:33])=[CH:31][CH:32]=5)[CH2:24]4)=[O:22])=[CH:16][CH:15]=3)[CH:11]=[N:10]2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[O:34]1[CH2:37][C:36](=O)[CH2:35]1.C([BH3-])#N.[Na+]>CO>[CH3:1][C:2]1([CH2:8][N:9]2[CH:13]=[C:12]([C:14]3[CH:15]=[CH:16][C:17]([NH:20][C:21]([CH:23]4[CH2:26][N:25]([C:27]5[N:28]=[N:29][C:30]([CH3:33])=[CH:31][CH:32]=5)[CH2:24]4)=[O:22])=[CH:18][CH:19]=3)[CH:11]=[N:10]2)[CH2:7][CH2:6][N:5]([CH:36]2[CH2:37][O:34][CH2:35]2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 150242543-OxetanoneHCID 86702117HCID 86702117, compound

Product 1

HCID 86702116HCID 86702116, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(4-(1-((4-Methylpiperidin-4-yl)methyl)-1H-pyrazol-4-yl)phenyl)-1-(6-methylpyridazin-3-yl)azetidine-3-carboxamide was dissolved in methanol (3 ml) and treated with oxetan-3-one (0.022 ml, 0.338 mmol) and sodium cyanoborohydride (0.021 g, 0.338 mmol) and stiffed overnight. The mixture was concentrated, purified by normal phase chromatography, triturated with ether and concentrated to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.09 (s, 1H), 8.05 (s, 1H), 7.82 (s, 1H), 7.64-7.58 (m, 2H), 7.56-7.49 (m, 2H), 7.29 (d, J=9.1 Hz, 1H), 6.80 (d, J=9.0 Hz, 1H), 4.51 (t, J=6.4 Hz, 2H), 4.40 (t, J=5.8 Hz, 2H), 4.20 (t, J=8.3 Hz, 2 H), 4.12 (dd, J=7.9, 6.1 Hz, 2H), 3.98 (s, 2H), 3.73 (tt, J=8.5, 6.1 Hz, 1H), 3.48-3.39 (m, 1H), 2.44 (s, 3 H), 2.42-2.33 (m, 2H), 2.16-1.99 (m, 2H), 1.58-1.46 (m, 2H), 1.30 (d, J=12.6 Hz, 2H), 0.89 (s, 3 H); MS (ESI(+)) m/e 502 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by normal phase chromatography
  3. customtriturated with ether
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-aa278e550a9447f89394267aa310e561
Source dataset
uspto-grants-2015_03
Patent number
US08975398B2

Reaction notes

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