Diisopropylethylamine → HCID 118162182, compound

HRID 1749440Notes

Reaction equation

[OH:1][CH2:2][C@H:3]1[CH2:6][C@@H:5]([NH:7][C:8]2[C:13]([C:14]#[N:15])=[CH:12][N:11]=[C:10](S(C)(=O)=O)[N:9]=2)[C:4]1([CH3:21])[CH3:20].OC[C@H]1C[C@@H](NC2C(C#N)=CN=C(S(C)=O)N=2)C1(C)C.Cl.[F:43][C:44]([F:54])([F:53])[C:45]1[CH:50]=[CH:49][N:48]=[CH:47][C:46]=1[CH2:51][NH2:52].CCN(C(C)C)C(C)C>C(O)C>[OH:1][CH2:2][C@H:3]1[CH2:6][C@@H:5]([NH:7][C:8]2[C:13]([C:14]#[N:15])=[CH:12][N:11]=[C:10]([NH:52][CH2:51][C:46]3[CH:47]=[N:48][CH:49]=[CH:50][C:45]=3[C:44]([F:54])([F:43])[F:53])[N:9]=2)[C:4]1([CH3:21])[CH3:20]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-(((1R,3S)-3-(hydroxymethyl)-2,2-dimethylcyclobutyl)amino)-2-(methylsulfonyl)pyrimidine-5-carbonitrile and 4-(((1R,3S)-3-(hydroxymethyl)-2,2-dimethylcyclobutyl)amino)-2-(methylsulfinyl)pyrimidine-5-carbonitrile (1.0 equiv.), (4-(trifluoromethyl)pyridin-3-yl)methanamine hydrochloride (1.0 equiv.) and DIEA (3.0 equiv.) was combined in ethanol (0.1 M) and heated to 80° C. After 2 h, the reaction mixed was worked up using standard methods to afford the title compound (45% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm) 8.71 (d, J=5.08 Hz, 1H), 8.57-8.65 (m, 1H), 8.15-8.25 (m, 2H), 7.65-7.75 (m, 1H), 7.19-7.32 (m, 1H), 4.70 (d, J=5.08 Hz, 2H), 4.23 (t, J=4.88 Hz, 1H), 3.96 (q, J=8.33 Hz, 1H), 3.20-3.29 (m, 1H), 1.73-1.96 (m, 2H), 1.53-1.68 (m, 1H), 1.20 (s, 1H), 0.86 (s, 1H), 0.62-0.77 (m, 6H): MS(ESI) m/z 407.3[M+1]+.

Workup

additionthe reaction mixed

Sources & evidence

ORD record: ord-c7ea9f3525c84c568ffdf7f5fea022c3
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156798B2

Reaction notes

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