Nicotinic Acid → HCID 59451444, compound

HRID 1874824Notes

Reaction equation

FC(F)(F)C(O)=O.[NH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([NH:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([O:29][C:30]3[CH:35]=[C:34]([C:36]#[N:37])[CH:33]=[C:32]([Cl:38])[CH:31]=3)[C:23]=1[F:39])=[O:19])=[CH:12]2.[N:40]1[CH:45]=[CH:44][CH:43]=[C:42]([C:46](O)=[O:47])[CH:41]=1.CCN(C(C)C)C(C)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][NH:20][C:18]([C:13]2[NH:14][C:15]3[C:11]([CH:12]=2)=[CH:10][C:9]([NH:8][C:46]([C:42]2[CH:41]=[N:40][CH:45]=[CH:44][CH:43]=2)=[O:47])=[CH:17][CH:16]=3)=[O:19])=[C:23]([F:39])[C:24]=1[O:29][C:30]1[CH:35]=[C:34]([C:36]#[N:37])[CH:33]=[C:32]([Cl:38])[CH:31]=1

Participants

Reactant 4

HCID 938Nicotinic Acid

HCID 81531Diisopropylethylamine

HCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chloride

HCID 866448845-amino-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1H-indole-2-carboxamide trifluoroacetate

Product 1

HCID 59451444HCID 59451444, compoundYield 22.3%

Procedure

The title compound (0.011 g, 19%) was prepared from 5-amino-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1H-indole-2-carboxamide trifluoroacetate (0.050 g, 0.086 mmol), 3-pyridinecarboxylic acid (0.011 g, 0.086 mmol), DIPEA (0.075 mL, 0.43 mmol) and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (0.065 g, 0.257 mmol) in a similar manner as described in the general procedure. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.66 (s, 1H), 10.38 (s, 1H), 9.16 (s, 2H), 8.80 (s, 1H), 8.38 (s, 1H), 8.12 (s, 1H), 7.72-7.97 (m, 1H), 7.32-7.97 (m, 7H), 7.19 (s, 1H), 4.58 (d, 2H). MS: m/z 574 (M+1).

Sources & evidence

ORD record: ord-b6ca32dc39d8497487e1c97be326a090
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304419B2

Reaction notes

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