Triethylamine → HCID 178491165, compound

HRID 1525209Notes

Reaction equation

[OH:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:3]=1.CCN(CC)CC.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[NH2:37][CH:38]([C:48]1[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[CH:50][CH:49]=1)[C:39]1[CH:44]=[CH:43][C:42]([PH:45](=[O:47])[OH:46])=[CH:41][CH:40]=1>C(#N)C>[OH:1][C:2]1[C:7]([C:8]([NH:37][CH:38]([C:48]2[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[CH:50][CH:49]=2)[C:39]2[CH:44]=[CH:43][C:42]([PH:45](=[O:46])[OH:47])=[CH:41][CH:40]=2)=[O:10])=[CH:6][N:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 4-hydroxy-2-(pyridin-2-yl)pyrimidine-5-carboxylic acid (1-1-h, 1.1 g, 5.1 mmol) in acetonitrile (20 ml) was added Et3N (1.02 g, 10.2 mmol). The mixture was aged for 15 min at room temperature. To the mixture was added CDI (800 mg, 5.1 mmol) and the resulting mixture was heated to 70° C. for 3 h. To the hot homogeneous solution was then added in one portion 4-(amino(4-methoxyphenyl)methyl)phenylphosphinic acid hydrochloride (1-1-e, 1.4 g, 5.1 mmol). Heating was continued for 2 h at 70° C. Then it was concentrated under vacuum and the residue was purified on prep-HPLC to provide the 1-1-6 (160 mg, 6%). 1H NMR (CD3OD, 300 MHz,): δ 13.35 (br, 1H), 8.80 (m, 1H), 8.62 (m, 2H), 8.45 (m, 1H), 7.23 (m, 7H), 7.79 (m, 2H), 6.52 (s, 1H), 6.25 (m, 1H), 3.70 (m, 3H).

Workup

temperatureHeating
waitwas continued for 2 h at 70° C
concentrationThen it was concentrated under vacuum
customthe residue was purified on prep-HPLC

Sources & evidence

ORD record: ord-22df340f1957490ca9ed45e61021e134
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079930B2

Reaction notes

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