Iodoethane → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(3-oxo-1H-pyrrolo[3,4-c]pyridin-2(3H)-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetic acid

HRID 879464Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:12]1[C:36]([CH3:37])=[CH:35][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([N:25]4[CH2:33][C:32]5[CH:31]=[CH:30][N:29]=[CH:28][C:27]=5[C:26]4=[O:34])[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:38]1[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].C(I)C>N1C=CC=CC=1>[C:1]([O:5][C@@H:6]([C:12]1[C:36]([CH3:37])=[CH:35][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([N:25]4[CH2:33][C:32]5[CH:31]=[CH:30][N:29]=[CH:28][C:27]=5[C:26]4=[O:34])[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:38]1[CH:39]=[CH:40][C:41]([Cl:44])=[CH:42][CH:43]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 170 °C

Procedure

To a solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(3-oxo-1H-pyrrolo[3,4-c]pyridin-2(3H)-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetate (28 mg, 0.044 mmol) in pyridine (2 mL) was added ethyl iodide (200 mg, excess). The reaction mixture was heated at 170° C. in microwave reactor for 90 minutes and the crude was concentrated and purified by reverse phase HPLC, eluting by 0-100% acetonitrile in H2O with 0.1% TFA to give the product. LCMS-ESI+: calc'd for C32H28ClN4O4S: 599.1 (M+H+); Found: 599.2 (M+H+). 1H NMR (400 MHz, CD3OD) δ: 8.80 (s, 1H), 8.58 (s, 2H), 8.18 (d, 1H), 7.57 (m, 2H), 7.50-7.43 (m, 4H), 7.33 (s, 1H), 5.14 (s, 1H), 4.68 (d, 2H), 2.33 (s, 3H), 0.90 (s, 9H).

Workup

concentrationthe crude was concentrated
custompurified by reverse phase HPLC
washeluting by 0-100% acetonitrile in H2O with 0.1% TFA
customto give the product

Sources & evidence

ORD record: ord-44781a0e659141088fff9527990497bf
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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