Triethylamine → 1,3-benzothiazol-2-yl(2-{[2-(1H-imidazol-4-yl)ethyl]amino}-4-pyrimidinyl)acetonitrile

HRID 2377591Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([C:13]1[CH:18]=[CH:17][N:16]=[C:15](Cl)[N:14]=1)[C:11]#[N:12].CCN(CC)CC.[NH2:27][CH2:28][CH2:29][C:30]1[N:34]=[CH:33][NH:32][CH:31]=1>CCO>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH:27][CH2:28][CH2:29][C:30]2[N:34]=[CH:33][NH:32][CH:31]=2)[N:14]=1)[C:11]#[N:12]

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of 1 (0.1 g, 0.35 mmol) in dry EtOH (3 ml) was added Et3N (0.05 ml, 0.35 mmol) and histamine (0.078 g, 0.70 mmol). After sonication, the yellow solution was shaken at 70° C. for 3 days. The yellow precipitate formed was filtered off and washed with H2O (2×) then EtOH (3×) and dried under vacuum at 40° C., affording 47 mg (37%) of the title compound as a bright yellow powder: mp 257-258° C., 10 was taken up in a mixture of DCM/TFA. The yellow fluffy solid formed by addition of ether was filtered off, washed with ether (3×) then dried under vacuum at 40° C., affording 36 mg (29%) of the title compound as a yellow powder: mp 247-249° C., MS: 362.0 (M+1); HPLC (Conditions a, 265 nm): 98%, rt. 2.87 min; 1H NMR (DMSO-d6): δ 14.25 (br s, 2H, exchangeable), 11.05 (br s, 1H, exchangeable), 9.03 (s, 1H), 7.94-7.87 (m, 1H), 7.74-7.71 (m, 2H), 7.57-7.52 (m, 2H), 7.42-7.37 (m, 1H), 7.24-7.19 (m, 1H), 6.40 (d, J=7.1 Hz, 1H), 3.97-3.55 (m, 3H), 3.11-3.05 (m, 2H).

Workup

customAfter sonication
customThe yellow precipitate formed
filtrationwas filtered off
washwashed with H2O (2×)
dry with materialEtOH (3×) and dried under vacuum at 40° C.

Sources & evidence

ORD record: ord-a776170df8064c38b732edcf45b9f044
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470686B2

Reaction notes

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