3-Phenylpropylamine → HCID 25182872, compound

HRID 2077493Notes

Reaction equation

HRID 2077493 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:20]=[CH:19][C:11]3[N:12]=[C:13]([NH:15]C(=O)C)[S:14][C:10]=3[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[C:21]1([CH2:27][CH2:28][CH2:29][NH2:30])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>N1C=CC=CC=1>[C:21]1([CH2:27][CH2:28][CH2:29][NH:30][C:2]2[N:7]=[C:6]([C:8]3[CH:20]=[CH:19][C:11]4[N:12]=[C:13]([NH2:15])[S:14][C:10]=4[CH:9]=3)[CH:5]=[CH:4][N:3]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 162593-PhenylpropylamineHCID 51357685N-(6-(2-Chloropyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide

Product 1

HCID 25182872HCID 25182872, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

N-(6-(2-chloropyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide (54.1 mg, 178 μmol) and 3-phenylpropylamine (25.2 μl, 178 μmol) were suspended in pyridine (0.80 mL) and sealed in a microwave vial and heated in the CEM microwave (CEM Corporation, Matthews, N.C.) at 120° C. and 300 watts with a 5 minute ramp time and 20-minute run time. The reaction was cooled to RT, concentrated, and the resulting crude material was purified on HPLC (10% to 95% MeCN/water with 0.1% TFA over 30 minutes) to afford 6-(2-(3-phenylpropylamino) pyrimidin-4-yl)benzo[d]thiazol-2-amine. MS (ESI pos. ion) m/z: 362. Calculated exact mass for C20H19N5S: 361.

Workup

  1. customsealed in a microwave vial
  2. temperatureThe reaction was cooled to RT
  3. concentrationconcentrated
  4. customthe resulting crude material was purified on HPLC (10% to 95% MeCN/water with 0.1% TFA over 30 minutes)

Sources & evidence

ORD record
ord-69b08bfa77d94a80ba1c274c199af0f6
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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