1-Chloropyrrolo[1,2-a]pyrazine → HCID 75204315, compound

HRID 1755250Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([NH:14][C@H:15]1[CH2:19][CH2:18][NH:17][CH2:16]1)=[O:13])[N:6]=[CH:5]2.Cl[C:21]1[C:22]2[N:23]([CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:25][N:26]=1>C(N(C(C)C)CC)(C)C.F[B-](F)(F)F.C([N+]1C=CN(C)C=1)CCC>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([NH:14][C@H:15]1[CH2:19][CH2:18][N:17]([C:21]3[C:22]4[N:23]([CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:25][N:26]=3)[CH2:16]1)=[O:13])[N:6]=[CH:5]2

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of the crude amine in 0.16 mL of diisopropylethylamine was added 1-chloropyrrolo[1,2-a]pyrazine (0.047 g, 0.31 mmol) followed by 1 drop of 1-butyl-3-methylimidazolium tetrafluorborate. The reaction was heated at 90° C. for 20 h. Purification of the residue by HPLC afforded (S)-6-chloro-N-(1-(pyrrolo[1,2-a]pyrazin-1-yl)pyrrolidin-3-yl)quinazoline-2-carboxamide (0.05 g, 0.013 mmol, 6%). 1H NMR (400 MHz, CD3OD) δ 9.60 (s, 1 H), 8.26(s, 1 H), 8.17 (d, J=9.1 Hz, 1 H), 8.07 (dd, J=1.8, 9.1 Hz, 1 H), 7.76 (d, J=1.5 Hz, 1 H), 7.72 (d, J=5.8 Hz, 1 H), 7.57 (s, 1 H), 6.93 (m, 1 H), 6.85 (d, J=5.8 Hz, 1 H), 5.06-4.84 (m, 1 H), 4.82-3.60 (br, 4 H), 2.65-2.40 (br, 2 H); MS: (ES) m/z calculated for C20H17ClN6O [M+H]+ 393.2, found 393.

Workup

customPurification of the residue by HPLC

Sources & evidence

ORD record: ord-6fc2c33efc944497aa40c32c7ac208b5
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169261B2

Reaction notes

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