Triethylamine → HCID 10457279, compound

HRID 1271888Notes

Reaction equation

HRID 1271888 reaction equation
C(O[C:6](=O)[NH:7][CH2:8][CH2:9][N:10]([CH:18]([C:22]1[N:31]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:30](=[O:39])[C:29]2[C:24](=[CH:25][C:26]([Cl:40])=[CH:27][CH:28]=2)[N:23]=1)[CH:19]([CH3:21])[CH3:20])[C:11](=[O:17])[C:12]([CH3:16])([CH3:15])CCl)(C)(C)C.C(OC(=O)NCCNC(C1N(CC2C=CC=CC=2)C(=O)C2C(=CC(Cl)=CC=2)N=1)C(C)C)(C)(C)C.ClCC(C)(C)C(Cl)=O.CCN(CC)CC>C(Cl)Cl>[CH2:32]([N:31]1[C:30](=[O:39])[C:29]2[C:24](=[CH:25][C:26]([Cl:40])=[CH:27][CH:28]=2)[N:23]=[C:22]1[CH:18]([N:10]1[C:11](=[O:17])[C:12]([CH3:16])([CH3:15])[CH2:6][NH:7][CH2:8][CH2:9]1)[CH:19]([CH3:20])[CH3:21])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 613453-Chloro-2,2-dimethylpropanoyl chlorideHCID 18455022HCID 18455022, compoundHCID 69476156HCID 69476156, compound

Product 1

HCID 10457279HCID 10457279, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Preparation of {2-[[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propyl]-(3-chloro-2,2-dimethyl-propanoyl)-amino]-ethyl}-carbamic acid tert-butyl ester: {2-[1-(3-Benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propylamino]-ethyl}-carbamic tert-butyl ester (450 mg, 0.93 mmol) was treated with 3-chloropivaloyl chloride (360 μL, 2.80 mmol) and Et3N (388 μl, 2.80 mmol) in CH2Cl2 (10 mL) at room temperature. After 48 h, the mixture was diluted with CH2Cl2 (10 mL), washed with water, brine, dried and concentrated under vacuum. Purification by flash chromatography on silica gel (3–6% EtOAc in hexane) gave the title compound (413 mg) as a clear oil: MS (ES) m/e 603 (M+H)+.

Workup

  1. washwashed with water, brine
  2. customdried
  3. concentrationconcentrated under vacuum
  4. customPurification by flash chromatography on silica gel (3–6% EtOAc in hexane)

Sources & evidence

ORD record
ord-1a8ae4e280914f928840be6ba0abcda6
Source dataset
uspto-grants-2007_04
Patent number
US07208487B2

Reaction notes

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