HCID 86634007, compound → HCID 66830178, compound

HRID 1041338Notes

Reaction equation

HRID 1041338 reaction equation
[Cl:1][C:2]1[C:3]([NH:28][C:29]2[CH:38]=[CH:37][CH:36]=[CH:35][C:30]=2[C:31]([NH:33][CH3:34])=[O:32])=[N:4][C:5]([NH:8][C:9]2[CH:27]=[CH:26][C:12]3[N:13](C(=O)C(F)(F)F)[CH2:14][CH2:15][C:16](=[O:19])[NH:17][CH2:18][C:11]=3[CH:10]=2)=[N:6][CH:7]=1>CCO>[Cl:1][C:2]1[C:3]([NH:28][C:29]2[CH:38]=[CH:37][CH:36]=[CH:35][C:30]=2[C:31]([NH:33][CH3:34])=[O:32])=[N:4][C:5]([NH:8][C:9]2[CH:27]=[CH:26][C:12]3[NH:13][CH2:14][CH2:15][C:16](=[O:19])[NH:17][CH2:18][C:11]=3[CH:10]=2)=[N:6][CH:7]=1

Participants

3

Reactant 1

HCID 86634007HCID 86634007, compound

Product 1

HCID 66830178HCID 66830178, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

2-{5-Chloro-2-[4-oxo-1-(2,2,2-trifluoro-acetyl)-1,2,3,4,5,6-hexahydro-benzo[b][1,5]diazocin-8-ylamino]-pyrimidin-4-ylamino}-N-methyl-benzamide (23 mg, 0.05 mmol) was dissolved in 1/1 EtOH/30% NaOH (2 ml) and heated to 80° C. in the microwave for 10 min. Reaction mixture was neutralized, extracted with CH2Cl2, dried over MgSO4, filtered, and concentrated to afford title compound as an off-white solid (5 mg, 26%) mp 267-268° C.; LCMS: m/z=452.30 (M+H+), HPLC (98% purity); 1H NMR (400 MHz, DMSO-d6) δ 11.61 (s, 1H), 9.21 (s, 1H), 8.72 (m, 2H), 8.16 (s, 1H), 7.73 (m, 1H), 7.47 (m, 2H), 7.32 (m, 2H), 7.11 (m, 1H), 6.73 (m, 1H), 5.74 (m, 1H), 4.18 (m, 2H), 3.23 (m, 2H), 2.73 (m, 3H), 2.65 (m, 2H).

Workup

  1. customReaction mixture
  2. extractionextracted with CH2Cl2
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0039fbb62b0e475b90060715e265715d
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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