Acrylic Acid → HCID 86721858, compound

HRID 1522290Notes

Reaction equation

HRID 1522290 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[F:10][C:11]([F:29])([F:28])[C:12]1[CH:13]=[C:14]([CH:25]=[CH:26][CH:27]=1)[O:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.[NH2:30][CH2:31][C:32]1([C:45]([OH:47])=[O:46])[CH2:37][CH2:36][N:35]([C:38]([O:40]C(C)(C)C)=O)[CH2:34][CH2:33]1.[C:48](O)(=O)[CH:49]=C>>[C:38]([N:35]1[CH2:34][CH2:33][C:32]([CH2:31][NH:30][C:7]2[C:2]([C:19]3[CH:20]=[CH:21][C:16]([O:15][C:14]4[CH:25]=[CH:26][CH:27]=[C:12]([C:11]([F:29])([F:28])[F:10])[CH:13]=4)=[CH:17][CH:18]=3)=[C:3]([NH2:9])[N:4]=[CH:5][N:6]=2)([C:45]([OH:47])=[O:46])[CH2:37][CH2:36]1)(=[O:40])[CH:48]=[CH2:49]

Participants

5

Reactant 4

HCID 6581Acrylic AcidHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 57978431B-[4-[3-(Trifluoromethyl)phenoxy]phenyl]boronic acidHCID 710891631-(1,1-Dimethylethyl) 4-(aminomethyl)-1,4-piperidinedicarboxylate

Product 1

HCID 86721858HCID 86721858, compoundYield 11.2%

Procedure

1-acryloyl-4-(((6-amino-5-(4-(3-(trifluoromethyl)phenoxy)phenyl)pyrimidin-4-yl)amino)methyl)piperidine-4-carboxylic acid was prepared 5,6-dichloropyrimidin-4-amine, (4-(3-(trifluoromethyl)phenoxy)phenyl)boronic acid, 4-(aminomethyl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid and acrylic acid with method S1, S2, S3, S4A. Yield 11.2%. 1H NMR (DMSO-d6) δ 8.31 (s, 1H), 7.25-7.75 (m, 8H), 7.03 (br., 2H), 6.77 (m, 1H), 6.62 (s, 1H), 6.04 (d, 1H), 5.60 (d, 1H), 4.12 (m, 1H), 3.83 (m, 1H), 2.75 (m, 1H), 1.91 (m, 2H), 1.28 (m, 2H). HPLC PURITY: 98%, MS: m/z=542[M+H]+

Sources & evidence

ORD record
ord-120ca27b71a34e818c326259204d9be8
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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