Acetic Acid → HCID 67111545, compound

HRID 1177642Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([NH2:26])[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.[C:27]([O:30][C@H:31]1[CH2:36][C:35](=[O:37])[O:34][C:32]1=[O:33])(=[O:29])[CH3:28].C(O)(=O)C>C1C=CC=CC=1>[C:27]([O:30][C@@H:31]([CH2:36][C:35]([NH:26][C:4]1[CH:5]=[CH:6][C:7]([C:8]2[S:9][C:10]3[C:15]([N:16]=2)=[CH:14][CH:13]=[C:12]([C:17]2([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:18][CH2:19]2)[N:11]=3)=[C:2]([F:1])[CH:3]=1)=[O:37])[C:32]([OH:34])=[O:33])(=[O:29])[CH3:28]

Participants

Conditions

Temperature: 80 °C

Procedure

To 3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzenamine (70 mg, 0.194 mmol) and (S)-(−)-2-acetoxysuccinic anhydride (34 mg, 213 μmol) was added benzene (1.9 mL) and acetic acid (55 μl, 0.968 mmol) before it was stirred at 80° C. for 1 h. The reaction mixture was concentrated before the regioisomers were separated via SFC (Column: Chiralpak IC, Mobile Phase: liquid CO2/40% MeOH) to give (2S)-2-acetoxy-4-(3-fluoro-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)phenylamino)-4-oxobutanoic acid. MS (ESI) m/z: Calculated: 519.1; Observed: 520.1 (M++H).

Workup

concentrationThe reaction mixture was concentrated before the regioisomers
customwere separated via SFC (Column: Chiralpak IC, Mobile Phase: liquid CO2/40% MeOH)

Sources & evidence

ORD record: ord-5de795aa9e4a4677abbd83b23bcbfcb8
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

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