Benzylamine → HCID 59924918, compound

HRID 2300787Notes

Reaction equation

HRID 2300787 reaction equation
[C:1]1([C@@H:7]([NH:9]C2N=C(N3C4C=CC(C(O)=O)=CC=4N=C3)C=CN=2)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:28]1([C@@H:34]([NH:36][C:37]2[N:42]=[C:41]([N:43]3[C:47]4[CH:48]=[C:49]([C:52]([OH:54])=O)[CH:50]=[CH:51][C:46]=4[N:45]=[CH:44]3)[CH:40]=[CH:39][N:38]=2)[CH3:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N)C1C=CC=CC=1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[C:28]1([C@@H:34]([NH:36][C:37]2[N:42]=[C:41]([N:43]3[C:47]4[CH:48]=[C:49]([C:52]([NH:9][CH2:7][C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)=[O:54])[CH:50]=[CH:51][C:46]=4[N:45]=[CH:44]3)[CH:40]=[CH:39][N:38]=2)[CH3:35])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

7

Reactant 5

HCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69960995HCID 69960995, compoundHCID 69961483HCID 69961483, compound

Product 1

HCID 59924918HCID 59924918, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of a mixture 10 mg (0.028 mmol) of 2-[(S)-1-phenylethylamino]-4-[5-carboxy-benzimidazol-1-yl]pyrimidine and 2-[(S)-1-phenylethylamino]-4-[6-carboxy-benzimidazol-1-yl]pyrimidine (EXAMPLE 106 Step C) and benzylamine (0.003 mL, 0.028 mmol) in 0.6 mL CH2Cl2 was added N-methylmopholine (0.004 mL) followed by 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (10 mg). The solution was stirred for 4 hours then quenched with water. The organic fraction was concentrated and the product purified by chromatography to afford the title compounds. Partial 1H NMR (500 MHz CD3OD): δ 8.73 (brs, 1H); 8.57 (brs, 1H); 8.33 (brs, 1H); 7.82 (d J=10 Hz, 1H); 7.70 (d J=10 Hz, 1H); 6.82 (brs, 1H); 6.63 (brs, 1H); 5.23 (br, 1H); 4.70 (d J=5.5 Hz, 2H); 1.63 (d J=6.5 Hz, 3H). Partial 1H NMR (500 MHz CD3OD): δ 8.47 (br, 1H); 8.36 (br, 1H); 8.20 (s, 1H); 6.79 (d J=5.5 Hz, 1H); 6.60 (br, 1H); 5.18 (br, 1H); 4.72 (d J=5.5 Hz, 2H); 1.62 (d, J=6.5 Hz, 3H).

Workup

  1. customthen quenched with water
  2. concentrationThe organic fraction was concentrated
  3. customthe product purified by chromatography

Sources & evidence

ORD record
ord-0ba6f67b95364cbd918bead01941f4ce
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

Loading…