Sodium Hydroxide → HCID 68637190, compound

HRID 640002Notes

Reaction equation

HRID 640002 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[F:29][C:30]1[CH:31]=[C:32]([NH:36][C:37](=[O:62])[CH2:38][N:39]2[CH:43]=[C:42]([NH:44][C:45]3[C:54]4[C:49](=[CH:50][C:51]([O:55][CH2:56][CH:57]5[CH2:61][CH2:60][NH:59][CH2:58]5)=[CH:52][CH:53]=4)[N:48]=[CH:47][N:46]=3)[CH:41]=[N:40]2)[CH:33]=[CH:34][CH:35]=1.[Si:63]([O:70][CH2:71][CH:72]=O)([C:66]([CH3:69])([CH3:68])[CH3:67])([CH3:65])[CH3:64].[OH-].[Na+]>O1CCCC1.CO.C(O)(=O)C>[Si:63]([O:70][CH2:71][CH2:72][N:59]1[CH2:60][CH2:61][CH:57]([CH2:56][O:55][C:51]2[CH:50]=[C:49]3[C:54]([C:45]([NH:44][C:42]4[CH:41]=[N:40][N:39]([CH2:38][C:37]([NH:36][C:32]5[CH:33]=[CH:34][CH:35]=[C:30]([F:29])[CH:31]=5)=[O:62])[CH:43]=4)=[N:46][CH:47]=[N:48]3)=[CH:53][CH:52]=2)[CH2:58]1)([C:66]([CH3:69])([CH3:68])[CH3:67])([CH3:65])[CH3:64]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86761076HCID 86761076, compound

Product 1

HCID 68637190HCID 68637190, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium triacetoxyborohydride (0.23 g, 1.1 mmol) was added to a mixture of N-(3-fluorophenyl)-2-(4-{[7-(pyrrolidin-3-ylmethoxy)quinazolin-4-yl]amino}-1H-pyrazol-1-yl)acetamide bis(trifluoroacetate) (0.30 g, 0.44 mmol) and (tert-butyldimethylsilyloxy)acetaldehyde (0.20 ml, 1.0 mmol) in tetrahydrofuran (9 ml) and methanol (3 ml) containing a catalytic amount of acetic acid. The mixture was stirred at room temperature for 1 hour. The mixture was poured into sodium hydroxide solution (1M) and extracted with dichloromethane. The organic layer was separated, washed with brine, dried over magnesium sulphate and then evaporated to leave a brown oil which was purified by silica gel chromatography. Elution with 3 to 6% methanol in dichloromethane gave 2-{4-[(7-{[1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)pyrrolidin-3-yl]methoxy}quinazolin-4-yl)amino]-1H-pyrazol-1-yl}-N-(3-fluorophenyl)acetamide. MS (+ve ESI): 620 (M+H)+.

Workup

  1. extractionextracted with dichloromethane
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customto leave a brown oil which
  7. customwas purified by silica gel chromatography
  8. washElution with 3 to 6% methanol in dichloromethane

Sources & evidence

ORD record
ord-695cc66bbb874baa823fa537bc940163
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Reaction notes

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