Benzyl isocyanate → HCID 67298325, compound

HRID 1520358Notes

Reaction equation

[CH2:1]([NH:8][C:9](=[O:37])[O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[C:16]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[N:15]=[C:14]2[NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34](=[O:36])[NH2:35])[C:2]1C=CC=CC=1.N(CC1C=CC=CC=1)=C=O>>[CH2:1]([NH:8][C:9](=[O:37])[O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[C:16]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[N:15]=[C:14]2[NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34](=[O:36])[NH2:35])[CH3:2]

Participants

Reactant 2

HCID 76639Benzyl isocyanate

HCID 67298380HCID 67298380, compound

Product 1

HCID 67298325HCID 67298325, compound

Procedure

4-(2-carbamoylphenylamino)-2-(pyridin-3-yl)quinazolin-6-yl ethylcarbamate was synthesized in a similar manner to that described for 4-(2-carbamoylphenylamino)-2-(pyridin-3-yl)quinazolin-6-yl benzylcarbamate substituting isocyanatoethane for (isocyanatomethyl)benzene. The resulting product was analyzed by LCMS: rt=1.11 min, [M+1]+=429.0, 1H-NMR (400 MHz, DMSO-d6): δ 13.06 (s, 1H), 9.66 (s, 1H), 9.10 (d, J=8.3 Hz, 1H), 8.87-8.80 (m, 2H), 8.51 (s, 1H), 8.06-7.94 (m, 4H), 7.88 (s, 1H), 7.79-7.63 (m, 3H), 7.24 (t, J=7.6 Hz, 1H), 3.22-3.11 (m, 2H), 1.14 (t, J=7.2 Hz, 3H).

Workup

customrt=1.11 min, [M+1]+=429.0, 1H-NMR (400 MHz, DMSO-d6): δ 13.06 (s, 1H), 9.66 (s, 1H), 9.10 (d, J=8.3 Hz, 1H), 8.87-8.80 (m, 2H), 8.51 (s, 1H), 8.06-7.94 (m, 4H), 7.88 (s, 1H), 7.79-7.63 (m, 3H), 7.24 (t, J=7.6 Hz, 1H), 3.22-3.11 (m, 2H), 1.14 (t, J=7.2 Hz, 3H)

Sources & evidence

ORD record: ord-39b5586f353a43fcac4d0b6667f3e8dd
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073890B2

Reaction notes

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