Pyrrolidine → HCID 178419924, compound

HRID 1982938Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[CH:12]=[C:13]3[C:19]([C:20]4[NH:24][C:23]5C=[CH:26][CH:27]=[C:28](CO)[C:22]=5[N:21]=4)=[N:18][NH:17][C:14]3=[N:15][CH:16]=2)=[CH:3][N:2]=1.[CH3:31][CH2:32][N:33]([CH:37]([CH3:39])C)[CH:34]([CH3:36])C.CS(Cl)(=O)=O.N1CCCC1>C1COCC1>[N:33]1([CH2:32][C:31]2[C:23]3[N:24]=[C:20]([C:19]4[C:13]5[C:14](=[N:15][CH:16]=[C:11]([C:4]6[C:5]7[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=7)[CH:1]=[N:2][CH:3]=6)[CH:12]=5)[NH:17][N:18]=4)[NH:21][C:22]=3[CH:28]=[CH:27][CH:26]=2)[CH2:34][CH2:36][CH2:39][CH2:37]1

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of Compound 3 (30 mg, 0.08 mmol) and DIPEA (28 μl, 0.36 mmol) in dry THF (1 mL) was cooled to 0° C. Methanesulfonyl chloride (18 μl, 0.23 mmol) was added dropwise and the mixture was stirred at 0° C. for 3 hours. Pyrrolidine (32 μl 0.39 mmol) was added and the suspension was gradually warmed to room temperature and stirred for 2 hours. The reaction was quenched with water (0.1 mL) and the solvent was removed in vacuo. The crude product was purified by silica gel chromatography to give Compound 7 (13 mg, 38%) as a yellow powder. 1H NMR (300 MHz MeOD) δ 9.36 (s, 1H), 9.10 (d, 1H, J=2.1 Hz), 8.78 (d, 1H, J=2.1 Hz), 8.55 (s, 1H), 8.27 (d, 1H, J=7.8 Hz), 7.95 (m, 1H), 7.83 (m, 2H), 7.72 (dd, 1H, J=1.8, 7.2 Hz), 7.39 (m, 2H), 4.75 (s, 2H), 3.38 (b, 4H), 2.01 (b, 4H); MS (ESI) m/z: 446 (M+H+).

Workup

temperaturethe suspension was gradually warmed to room temperature
stirringstirred for 2 hours
customThe reaction was quenched with water (0.1 mL)
customthe solvent was removed in vacuo
customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record: ord-a6fa982fe3d94c78b3c86c22de8eba0d
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07541367B2

Reaction notes

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