HCID 118251003, compound → HCID 118251408, compound

HRID 2283463Notes

Reaction equation

HRID 2283463 reaction equation
BrC1C=C(N[C@@H]2CCCN(C(OC(C)(C)C)=O)C2)C(OC)=NC=1.[Cl:24][CH2:25][C:26]([N:28]1CC[CH2:31][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]>>[Cl:24][CH2:25][C:26]([N:28]1[CH2:29][CH:30]([NH:34][C:35]2[C:40](=[O:41])[NH:39][CH:38]=[C:37]([C:42]3[CH:43]=[CH:44][N:45]=[CH:46][CH:47]=3)[CH:36]=2)[CH2:31]1)=[O:27]

Participants

3

Reactant 2

HCID 118251003HCID 118251003, compoundHCID 118251036HCID 118251036, compound

Product 1

HCID 118251408HCID 118251408, compound

Procedure

Following Example 1, but using tert-butyl 3-aminoazetidine-1-carboxylate (Example 1 Step 3) and reaction with chloroacetyl chloride (Example 1 Step 6) provided the desired compound after purification: 1H NMR (300 MHz, DMSO-d6) 11.87 (br s, 1H), 8.52 (d, J=5.4 Hz, 2H), 7.61 (d, J=6.0 Hz, 2H), 7.25-7.40 (m, 1H), 6.45-6.55 (m, 1H), 6.27 (d, J=6.3 Hz, 1H), 4.86 (apparent t, J=7.7 Hz, 1H), 4.25-4.44 (m, 2H), 4.13 (narrow m, 2H), 4.00-4.25 (m, 1H), 3.85-4.00 (m, 1H); MS (ES) m/z 319 (M+H).

Sources & evidence

ORD record
ord-bfcd29a823154bd0a1993b13b83c8555
Source dataset
uspto-grants-2015_09
Patent number
US09145393B2

Reaction notes

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