Diisopropylethylamine → HCID 67111735, compound

HRID 1177657Notes

Reaction equation

HRID 1177657 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].C(N(C(C)C)CC)(C)C.[F:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[C:27]1[S:28][C:29]2[C:34]([N:35]=1)=[CH:33][CH:32]=[C:31]([C:36]1([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH2:38][CH2:37]1)[N:30]=2)[CH:22]=O.[Na]>CO.CCOC(C)=O.C(Cl)(Cl)Cl>[F:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[C:27]1[S:28][C:29]2[C:34]([N:35]=1)=[CH:33][CH:32]=[C:31]([C:36]1([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH2:37][CH2:38]1)[N:30]=2)[CH2:22][NH:7][CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:8]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 5360545SodiumHCID 591749073-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde

Product 1

HCID 67111735HCID 67111735, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

Glycine ethyl ester hydrochloride (224 mg, 1.602 mmol) was dissolved in MeOH (4.0 mL) and chloroform (4.0 mL) before diisopropylethylamine (279 μL, 1.602 mmol) was added and stirred at ambient temperature for 15 min. 3-Fluoro-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)benzaldehyde (300 mg, 0.801 mmol) and sodium triacetoxyhydroborate (340 mg, 1.602 mmol) were then added and stirred at ambient temperature for 24 h. The reaction mixture was diluted with 100 mL of EtOAc, added to a separatory funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed 1 time with 50 mL of ammonium chloride (saturated, aqueous), separated, dried over sodium sulfate, and concentrated via rotovap to give ethyl 2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo-[5,4-b]pyridin-2-yl)benzylamino)acetate after flash chromatography. MS (ESI) m/z: Calculated: 461.2; Observed: 461.9 (M++H).

Workup

  1. stirringstirred at ambient temperature for 24 h
  2. additionadded to a separatory funnel
  3. custompartitioned with sodium bicarbonate (saturated, aqueous)
  4. washwashed 1 time with 50 mL of ammonium chloride (saturated, aqueous)
  5. customseparated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated via rotovap

Sources & evidence

ORD record
ord-ac64b47430114b33957009fd46d4d5f7
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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