Sodium Bicarbonate → HCID 67443027, compound

HRID 1400925Notes

Reaction equation

HRID 1400925 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7]C(=O)OC(C)(C)C)[CH2:3][CH2:2]1.[CH:15]1([NH:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]3[CH:34]=[CH:33][N:32]=[C:31]4[CH:35]=[C:36]([C:38]5[CH:43]=[CH:42][C:41]([CH:44]=O)=[CH:40][N:39]=5)[S:37][C:30]=34)=[C:24]([F:46])[CH:23]=2)=[O:20])[CH2:17][CH2:16]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>CN1C(=O)CCC1.CC(O)=O>[NH2:7][CH:4]1[CH2:3][CH2:2][N:1]([CH2:44][C:41]2[CH:42]=[CH:43][C:38]([C:36]3[S:37][C:30]4[C:31](=[N:32][CH:33]=[CH:34][C:29]=4[O:28][C:25]4[CH:26]=[CH:27][C:22]([NH:21][C:19]([NH:18][CH:15]5[CH2:16][CH2:17]5)=[O:20])=[CH:23][C:24]=4[F:46])[CH:35]=3)=[N:39][CH:40]=2)[CH2:6][CH2:5]1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 582365791-Cyclopropyl-3-(3-fluoro-4-(2-(5-formylpyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)urea

Product 1

HCID 67443027HCID 67443027, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

tert-Butyl piperidin-4-ylcarbamate (1.34 g, 6.69 mmol) was added to a solution of the aldehyde 47 (2.0 g, 4.46 mmol) in a mixture of NMP (20 mL) and glacial AcOH (0.250 mL). The reaction mixture was stirred for 30 min. NaBH(OAc)3 was then added and the reaction mixture was stirred for an additional 2.5 hours. The reaction mixture was then poured into a saturated aqueous NaHCO3 solution. A precipitate was formed which was collected by filtration, washed with water and air-dried. The crude material was purified by column chromatography using a 5 to 20% gradient of MeOH in EtOAc as eluent to afford the title compound 343 (1.45 g, 51.4% yield). MS (m/z): 633.6 (M+1)+.

Workup

  1. stirringthe reaction mixture was stirred for an additional 2.5 hours
  2. customA precipitate was formed which
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customair-dried
  6. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-99465bcc27c646c8afa8e1c926354fde
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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