HCID 118598908, compound → HCID 118598691, compound

HRID 1050390Notes

Reaction equation

HRID 1050390 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([NH:9][C:10]2[N:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]([CH:19]3[CH2:21][CH2:20]3)=[O:18])[CH:11]=2)[C:6](=[O:22])[N:5]2[C:23]3([CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[NH:24][C:25](=[O:26])[C:4]=12)=[O:2]>CO.O1CCCC1.[BH4-].[Na+].O>[OH:2][CH2:1][C:3]1[CH:8]=[C:7]([NH:9][C:10]2[N:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]([CH:19]3[CH2:20][CH2:21]3)=[O:18])[CH:11]=2)[C:6](=[O:22])[N:5]2[C:23]3([CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[NH:24][C:25](=[O:26])[C:4]=12

Participants

5

Reactant 1

HCID 118598908HCID 118598908, compound

Product 1

HCID 118598691HCID 118598691, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 4311764Sodium borohydrideSolventHCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of N-(6-((8′-formyl-1′,5′-dioxo-1′,5′-dihydro-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridin]-6′-yl)amino)pyrimidin-4-yl)cyclopropanecarboxamide (1.2 g, 2.85 mmol) in methanol/tetrahydrofuran (1:2, 30 mL), sodium borohydride was added portion wise at 0° C. The reaction mass was stirred at 0° C. for 2 h. After completion, the reaction mixture was diluted with water (100 mL) and the mixture was extracted with 10% methanol in dichloromethane (2×50 mL). The organics were then separated and dried (magnesium sulfate) and concentrated to dryness under vacuum to afford N-(6-((8′-(hydroxymethyl)-1′,5′-dioxo-1′,5′-dihydro-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridin]-6′-yl)amino)pyrimidin-4-yl)cyclopropanecarboxamide (5) as brown solid. Yield: 0.7 g, 62%; MS (ESI) m/z 423.43 [M−1]−; 1H NMR (400 MHz, DMSO-d6) δ 10.86 (s, 1H), 10.24-10.18 (m, 1H), 8.71-8.62 (m, 1H), 8.56-8.52 (m, 1H), 7.84 (s, 1H), 6.13-5.33 (m, 1H), 4.47-4.33 (m, 3H), 3.16-2.84 (m, 4H), 2.01-1.86 (m, 2H), 1.72-1.66 (m, 5H), 1.43-1.40 (m, 2H), 1.34-1.16 (m, 1H).

Workup

  1. extractionthe mixture was extracted with 10% methanol in dichloromethane (2×50 mL)
  2. customThe organics were then separated
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated to dryness under vacuum

Sources & evidence

ORD record
ord-5c308af830d8481ebeccc86293ffb16b
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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