HCID 66716044, compound → HCID 66715336, compound

HRID 2271887Notes

Reaction equation

HRID 2271887 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2[NH:17][C:18]1[CH:19]=[CH:20][C:21]([NH:24][CH:25]2[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26]2)=[N:22][CH:23]=1.[Cl:37][C:38]1[CH:43]=[C:42](B2OC(C)(C)C(C)(C)O2)[CH:41]=[C:40]([F:53])[C:39]=1[OH:54]>>[Cl:37][C:38]1[CH:43]=[C:42]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12]([CH:14]2[CH2:15][CH2:16]2)=[O:13])=[C:5]3[NH:17][C:18]2[CH:23]=[N:22][C:21]([NH:24][CH:25]3[CH2:29][CH2:28][NH:27][CH2:26]3)=[CH:20][CH:19]=2)[CH:41]=[C:40]([F:53])[C:39]=1[OH:54]

Participants

3

Reactant 2

HCID 66716044HCID 66716044, compoundHCID 667160792-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 66715336HCID 66715336, compoundYield 45%

Procedure

Following general procedure D, tert-butyl 3-(5-(6-bromo-3-(cyclopropanecarbonyl)quinolin-4-ylamino)pyridin-2-ylamino)pyrrolidine-1-carboxylate (100 mg, 0.18 mmol) was reacted with 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (73 mg, 0.27 mmol) to obtain the protected intermediate which was subjected to general procedure A-2 to afford the desired product (42 mg, 45% over 2 steps) as a yellow solid: NMR (500 MHz, MeOD+TFA-d) δ 9.40 (br s, 1H), 8.22 (dd, J=8.8, 2.0 Hz, 1H), 8.17-8.06 (m, 2H), 8.00 (d, J=8.8 Hz, 1H), 7.55 (dd, J=8.9, 2.7 Hz, 1H), 7.19-7.13 (m, 2H), 6.83-6.76 (m, 1H), 4.65-4.56 (m, 1H), 3.66-3.49 (m, 2H), 3.45-3.30 (m, 2H), 2.87 (br s, 1H), 2.48-2.37 (m, 1H), 2.19-2.08 (m, 1H), 1.28-1.16 (m, 4H). ESI MS m/z 518 [C28H25ClFN5O2+H]+; HPLC>99.0% (AUC), tR=10.43 min.

Workup

  1. customto obtain the protected intermediate which

Sources & evidence

ORD record
ord-5063a423bb9f466e8735279d53ea5251
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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