Allylamine → HCID 68460320, compound

HRID 2358801Notes

Reaction equation

HRID 2358801 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10](O)=[O:11])=[C:4]([NH:18][C:19]2[C:28]3[C:23](=[N:24][C:25]([CH3:29])=[CH:26][CH:27]=3)[N:22]=[CH:21][CH:20]=2)[CH:3]=1.CN1CCOCC1.ClC(OC(C)=C)=O.[CH2:44]([NH2:47])[CH:45]=[CH2:46]>C1COCC1>[CH2:44]([NH:47][C:10](=[O:11])[C:9]1[CH:13]=[CH:14][CH:15]=[C:7]([O:6][C:5]2[CH:16]=[CH:17][C:2]([Cl:1])=[CH:3][C:4]=2[NH:18][C:19]2[C:28]3[C:23](=[N:24][C:25]([CH3:29])=[CH:26][CH:27]=3)[N:22]=[CH:21][CH:20]=2)[CH:8]=1)[CH:45]=[CH2:46]

Participants

6

Reactant 4

HCID 7853AllylamineHCID 79724-MethylmorpholineHCID 93846Isopropenyl chloroformateHCID 68460621HCID 68460621, compound

Product 1

HCID 68460320HCID 68460320, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 208d (60 mg, 0.147 mmol) was dissolved in THF to which was added N-methyl morpholine (49 mg, 0.162 mmol), and isopropenyl chloroformate (36 mg, 0.295 mmol). This was stirred at room temperature for 1 hr at which time the allylamine (42 mg, 0.739 mmol) was added and the reaction mixture stirred at room temperature for another 1 hr. THF was then removed under a stream of N2 and then crude oil was purified by HPLC with TFA providing the product as a trifluoroacetic acid. (8.0 mg, 9.5%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.92 (s, 3H), 2.74 (s, 2 H), 3.86 (d, J=5.15 Hz, 2 H), 5.04-5.16 (m, 2 H), 5.73-5.98 (m, 1 H), 6.73 (d, J=6.99 Hz, 1 H), 7.10 (dd, J=7.72, 2.21 Hz, 1 H), 7.27-7.43 (m, 3 H), 7.51-7.65 (m, 2 H), 7.69-7.82 (m, 2H), 8.54 (d, J=7.35 Hz, 1 H), 8.82 (d, J=8.46 Hz, 1 H); MS (ESI+) m/z 445 (M+TFA+H)+; (ESI−) m/z 443 (M+TFA−H)−.

Workup

  1. additionwas added
  2. customTHF was then removed under a stream of N2
  3. customcrude oil was purified by HPLC with TFA providing the product as a trifluoroacetic acid

Sources & evidence

ORD record
ord-b70922b836584da0a04dc62d764d0b32
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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