HCID 118251003, compound → HCID 118250956, compound

HRID 2283464Notes

Reaction equation

Br[C:2]1C=C(N[C@@H]2CCCN(C(OC(C)(C)C)=O)C2)C(OC)=N[CH:7]=1.ClC[C:26]([N:28]1[CH2:33]CC[C@@H:30]([NH:34][C:35]2[C:40](=[O:41])[NH:39][CH:38]=[C:37]([C:42]3[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=3)[CH:36]=2)[CH2:29]1)=[O:27]>>[C:26]([N:28]1[CH2:33][CH:30]([NH:34][C:35]2[C:40](=[O:41])[NH:39][CH:38]=[C:37]([C:42]3[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=3)[CH:36]=2)[CH2:29]1)(=[O:27])[CH:2]=[CH2:7]

Participants

Reactant 2

HCID 118251003HCID 118251003, compound

HCID 118251036HCID 118251036, compound

Product 1

HCID 118250956HCID 118250956, compound

Procedure

Following Example 1, but using tert-butyl 3-aminoazetidine-1-carboxylate (Example 1 Step 3) and reaction with acroyl chloride (Example 1 Step 6) provided the desired compound after purification: 1H NMR (300 MHz, DMSO-d6) 11.86 (br s, 1H), 8.52 (d, J=6.3 Hz, 2H), 7.62 (dd, J=4.2, 1.5 Hz, 2H), 7.25-7.35 (m, 1H), 6.61 (d, J=2.1 Hz, 1H), 6.20-6.40 (m, 2H), 6.10 (dd, J=17.1, 2.4 Hz, 1H), 5.67 (dd, J=10.2, 2.1 Hz, 1H), 4.61 (apparent t, J=7.8 Hz, 1H), 4.25-4.45 (m, 2H), 4.05-4.15 (m, 1H), 3.80-3.95 (m, 1H); MS (ES) m/z 297 (M+H).

Sources & evidence

ORD record: ord-ce9cf7f6573f466796d518f664a2f43f
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145393B2

Reaction notes

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