Cyclopropanecarboxaldehyde → HCID 57386164, compound

HRID 407060Notes

Reaction equation

HRID 407060 reaction equation
[CH:1]1([CH:4]=O)[CH2:3][CH2:2]1.[C:6]([CH2:8][C:9]1([N:13]2[CH:17]=[C:16]([C:18]3[CH:23]=[N:22][N:21]4[C:24]([C:27]5[CH:28]=[C:29]([NH:33][C:34]([NH:36][CH2:37][C:38]([F:41])([F:40])[F:39])=[O:35])[CH:30]=[CH:31][CH:32]=5)=[CH:25][N:26]=[C:20]4[CH:19]=3)[CH:15]=[N:14]2)[CH2:12][NH:11][CH2:10]1)#[N:7].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[C:6]([CH2:8][C:9]1([N:13]2[CH:17]=[C:16]([C:18]3[CH:23]=[N:22][N:21]4[C:24]([C:27]5[CH:28]=[C:29]([NH:33][C:34]([NH:36][CH2:37][C:38]([F:40])([F:41])[F:39])=[O:35])[CH:30]=[CH:31][CH:32]=5)=[CH:25][N:26]=[C:20]4[CH:19]=3)[CH:15]=[N:14]2)[CH2:10][N:11]([CH2:4][CH:1]2[CH2:2][CH2:3]2)[CH2:12]1)#[N:7]

Participants

5

Reactant 3

HCID 123114CyclopropanecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67980375N-[3-(7-{1-[3-(cyanomethyl)azetidin-3-yl]-1H-pyrazol-4-yl]imidazo[1,2-b]pyridazin-3-yl)phenyl]-N'-(2,2,2-trifluoroethyl)urea

Product 1

HCID 57386164HCID 57386164, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cyclopropanecarboxaldehyde (4.2 mg, 0.060 mmol) was added to a mixture of N-[3-(7-{1-[3-(cyanomethyl)azetidin-3-yl]-1H-pyrazol-4-yl}imidazo[1,2-b]pyridazin-3-yl)phenyl]-N′-(2,2,2-trifluoroethyl)urea (15 mg, 0.030 mmol) in methanol (1.0 mL). After stirring at r.t. for 20 min, sodium triacetoxyborohydride (13 mg, 0.060 mmol) was added. The reaction mixture was stirred at r.t. for 4 h. The mixture was purified by RP-HPLC (pH=10) to afford the desired product. LCMS (M+H)+: m/z=550.2.

Workup

  1. stirringThe reaction mixture was stirred at r.t. for 4 h
  2. customThe mixture was purified by RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-27a2a253076a4c809ab290428991f696
Source dataset
uspto-grants-2014_06
Patent number
US08754114B2

Reaction notes

Loading…