Diisopropylethylamine → HCID 71269957, compound

HRID 1842824Notes

Reaction equation

[CH3:1][N:2]([CH2:10][CH2:11][NH:12][CH3:13])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].F[C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:18]([NH:24][C:25]2[N:30]=[C:29]([C:31]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[N:33]([CH3:40])[CH:32]=3)[CH:28]=[CH:27][N:26]=2)=[C:17]([O:41][CH3:42])[CH:16]=1.CCN(C(C)C)C(C)C>CC(N(C)C)=O.CCOC(C)=O>[CH3:42][O:41][C:17]1[C:18]([NH:24][C:25]2[N:30]=[C:29]([C:31]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[N:33]([CH3:40])[CH:32]=3)[CH:28]=[CH:27][N:26]=2)=[CH:19][C:20]([N+:21]([O-:23])=[O:22])=[C:15]([N:12]([CH3:13])[CH2:11][CH2:10][N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:6])([CH3:7])[CH3:8])[CH:16]=1

Participants

Conditions

Temperature: 100 °C

Procedure

tert-Butyl N-methyl-N-(2-methylaminoethyl)carbamate (Intermediate 173, 300 mg, 1.59 mmol) was added to a suspension of N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(1-methy-lindol-3-yl)pyrimidin-2-amine (Intermediate 129, 522 mg, 1.33 mmol) and DIPEA (0.462 mL, 2.65 mmol) in DMA (5 mL). The mixture was heated in a microwave at 100° C. for 4 h. The mixture was then diluted with EtOAc and washed with water (5×), brine, dried (MgSO4) and concentrated in vacuo. Purification by FCC, eluting with 0-2% CH3OH in CH2Cl2 gave the title compound (431 mg, 58%) as an orange solid after trituration with iii diethyl ether; 1H NMR: 1.37 (9H, s), 2.79 (3H, s), 2.88 (3H, s), 3.29-3.36 (2H, m), 3.39-3.44 (2H, m), 3.89 (3H, s), 3.99 (3H, s), 6.85 (1H, d), 7.14 (1H, t), 7.21-7.28 (2H, m), 7.53 (1H, br d), 8.04 (1H, s), 8.31-8.38 (3H, m), 8.72 (1H, br s); m/z: ES+ MH+ 562.35.

Workup

washwashed with water (5×), brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customPurification by FCC
washeluting with 0-2% CH3OH in CH2Cl2

Sources & evidence

ORD record: ord-a15129b202d44e12a77174ba1166d964
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946235B2

Reaction notes

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