Ethanolamine → HCID 90281418, compound

HRID 2170353Notes

Reaction equation

[F:1][CH:2]([F:48])[C:3]1[C:11]2[C:10]([F:13])([F:12])[CH2:9][CH2:8][C:7]([F:15])([F:14])[C:6]=2[N:5]([CH2:16][C:17]([NH:19][C@H:20]([C:30]2[C:35]([C:36]3[CH:37]=[CH:38][C:39]([F:45])=[C:40]([CH:44]=3)[C:41]([NH2:43])=[O:42])=[CH:34][N:33]=[C:32]([NH:46][CH3:47])[N:31]=2)[CH2:21][C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([F:29])[CH:23]=2)=[O:18])[N:4]=1.NC[CH2:51][OH:52].BrC1C([C@@H](NC(=O)CN2C3C(F)(F)CCC(F)(F)C=3C(C(F)F)=N2)CC2C=C(F)C=C(F)C=2)=NC(S(C)(=O)=O)=NC=1>>[F:48][CH:2]([F:1])[C:3]1[C:11]2[C:10]([F:12])([F:13])[CH2:9][CH2:8][C:7]([F:14])([F:15])[C:6]=2[N:5]([CH2:16][C:17]([NH:19][C@H:20]([C:30]2[C:35]([C:36]3[CH:37]=[CH:38][C:39]([F:45])=[C:40]([CH:44]=3)[C:41]([NH2:43])=[O:42])=[CH:34][N:33]=[C:32]([NH:46][CH2:47][CH2:51][OH:52])[N:31]=2)[CH2:21][C:22]2[CH:23]=[C:24]([F:29])[CH:25]=[C:26]([F:28])[CH:27]=2)=[O:18])[N:4]=1

Participants

Reactant 3

HCID 700Ethanolamine

HCID 90281331HCID 90281331, compound

HCID 90281385(S)-N-(1-(5-bromo-2-(methylsulfonyl)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)-2-(3-(difluoromethyl)-4,4,7,7-tetrafluoro-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetamide

Product 1

HCID 90281418HCID 90281418, compound

Procedure

The title compound (26) was prepared according to the method presented for the synthesis of compound 14B of Example 14 starting with 2-aminoethanol and 12C. 1H NMR (400 MHz, CD3OD) δ 8.83 (d, J=7.7 Hz, 1H), 8.06 (s, 2H), 7.49-7.32 (m, 2H), 7.21 (dd, J=10.7, 8.5 Hz, 1H), 7.02-6.58 (m, 2H), 6.45 (d, J=6.1 Hz, 2H), 5.22 (m, 1H), 5.05 (s, 2H), 3.86-3.58 (m, 4H), 3.18-2.85 (m, 2H), 2.66-2.23 (m, 4H). MS (m/z) 716.23 [M+H]+.

Sources & evidence

ORD record: ord-5ca650e677c747778459e2c40544e738
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09050344B2

Reaction notes

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