Acetic Anhydride → HCID 58529708, compound

HRID 1972840Notes

Reaction equation

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

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 58529326HCID 58529326, compound

Product 1

HCID 58529708HCID 58529708, compoundYield 41%

Procedure

5-(2-benzyl-2H-indazol-6-yl)-7-pyrrolidin-3-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine (40 mg, 0.098 mmol) was reacted with acetic anhydride (13 mg, 0.127 mmol) following the procedure of Example 107. The product was chromatographed on an ISCO® instrument (4 g column). The eluent was 0-6% (2N NH3 in methanol)/dichloromethane to yield 18 mg (41%) of desired product. 1H NMR (300 MHz, DMSO-d6) δ 8.62 (s, 1 H), 8.00-7.75 (m, 4 H), 7.60-7.40 (m, 4H), 7.23 (d, 1 H), 6.77 (d, 1 H), 5.72 (s, 2 H), 4.10-3.20 (m, 5H), 2.52-2.15 (m, 2H), 2.05 (s, 3 H); ES-MS m/z 452.4 [M+H]+, HPLC RT (min) 2.36.

Workup

customThe product was chromatographed on an ISCO® instrument (4 g column)

Sources & evidence

ORD record: ord-497e82e9a1c640c985de3686344d95cc
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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