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Acetic Acid → 1-((2,6-Dimethyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)-azetidine-3-carboxylic acid

HRID 1177453
Notes
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Reaction equation

HRID 1177453 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([C:10]2[S:11][C:12]3[C:17]([N:18]=2)=[CH:16][CH:15]=[C:14]([C:19]2([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:21][CH2:20]2)[N:13]=3)[CH:7]=[C:6]([CH3:28])[C:3]=1[CH:4]=O.[NH:29]1[CH2:32][CH:31]([C:33]([OH:35])=[O:34])[CH2:30]1.C(O)(=O)C.C([BH3-])#N.[Na+]>C(Cl)Cl.CO>[CH3:1][C:2]1[CH:9]=[C:8]([C:10]2[S:11][C:12]3[C:17]([N:18]=2)=[CH:16][CH:15]=[C:14]([C:19]2([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:20][CH2:21]2)[N:13]=3)[CH:7]=[C:6]([CH3:28])[C:3]=1[CH2:4][N:29]1[CH2:32][CH:31]([C:33]([OH:35])=[O:34])[CH2:30]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 931923-azetidinecarboxylic AcidHCID 5003444Sodium cyanoborohydrideHCID 866387112,6-Dimethyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde

Product 1

HCID 446009511-((2,6-Dimethyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)-azetidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2,6-dimethyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde (22.4 mg, 58.3 μmol), azetidine-3-carboxylic acid (29.5 mg, 291 μmol), and acetic acid (26.9 μl, 466 μmol) in 1:1 CH2Cl2/MeOH (2.0 mL) was stirred at 25° C. for 1 h. Sodium cyanoborohydride (6.59 mg, 105 μmol) was then added, and the resulting mixture was stirred at 25° C. for 15 h. The reaction mixture was then concentrated in vacuo, dissolved in 2 mL DMSO+20 μL trifluoroacetic acid, filtered, and purified by rpHPLC (10-100% acetonitrile/water+0.1% TFA) to provide 1-((2,6-dimethyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)-azetidine-3-carboxylic acid as a light yellow solid. MS (ESI) m/z: Calculated: 469.2; Observed: 470.1 (M++1).

Workup

  1. stirringthe resulting mixture was stirred at 25° C. for 15 h
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. dissolutiondissolved in 2 mL DMSO+20 μL trifluoroacetic acid
  4. filtrationfiltered
  5. custompurified by rpHPLC (10-100% acetonitrile/water+0.1% TFA)

Sources & evidence

ORD record
ord-22fd210a5366420f85895e5d23eac16e
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07842685B2

Reaction notes

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