HCID 118251003, compound → HCID 118251142, compound

HRID 2283462Notes

Reaction equation

HRID 2283462 reaction equation
BrC1C=C(N[C@@H]2CCCN(C(OC(C)(C)C)=O)C2)C([O:8]C)=NC=1.Cl[CH2:25][C:26]([N:28]1[CH2:33][CH2:32][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>>[C:33]([N:28]1[CH2:26][CH2:25][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:8])[CH:32]=[CH2:31]

Participants

3

Reactant 2

HCID 118251003HCID 118251003, compoundHCID 118251036HCID 118251036, compound

Product 1

HCID 118251142HCID 118251142, compound

Procedure

Following Example 1, but using (R)-tert-butyl 3-aminopyrrolidine-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=4.8 Hz, 2H), 7.64 (br s 2H), 7.28 (br s, 1H), 6.75 (d, J=7.2 Hz, 1H), 6.50-6.70 (m, 1H), 6.13 (d, J=16.8 Hz, 1H), 6.55-6.75 (m, 2H), 4.10-4.30 (m, 1H), 3.90-4.05 (m, 1H), 3.20-3.65 (m, 3H), 1.85-2.35 (m, 2H); MS (ES) m/z 311 (M+H).

Sources & evidence

ORD record
ord-99dc8e58eb38458997fa437c2e76d0a2
Source dataset
uspto-grants-2015_09
Patent number
US09145393B2

Reaction notes

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