Triethylamine → 1-(5-(3-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-5-chloropyridin-2-ylamino)pyridin-2-yl)-3-(4-(2-methoxyethoxy)phenyl)urea

HRID 1812100Notes

Reaction equation

HRID 1812100 reaction equation
[CH3:1][O:2][C:3]1[CH:41]=[CH:40][C:6]([CH2:7][N:8]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[C:17]([NH:23][C:24]4[CH:25]=[CH:26][C:27]([NH2:30])=[N:28][CH:29]=4)=[N:18][CH:19]=[C:20]([Cl:22])[CH:21]=3)[N:10]=2)=[CH:5][CH:4]=1.[CH3:42][O:43][CH2:44][CH2:45][O:46][C:47]1[CH:52]=[CH:51][C:50]([NH:53][C:54](=O)[O:55]C2C=CC([N+]([O-])=O)=CC=2)=[CH:49][CH:48]=1.CCN(CC)CC>C(Cl)Cl>[CH3:39][O:38][C:35]1[CH:34]=[CH:33][C:32]([CH2:31][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:41][CH:40]=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[C:17]([NH:23][C:24]4[CH:25]=[CH:26][C:27]([NH:30][C:54]([NH:53][C:50]5[CH:49]=[CH:48][C:47]([O:46][CH2:45][CH2:44][O:43][CH3:42])=[CH:52][CH:51]=5)=[O:55])=[N:28][CH:29]=4)=[N:18][CH:19]=[C:20]([Cl:22])[CH:21]=3)[N:10]=2)=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 666006494-Nitrophenyl 4-(2-methoxyethoxy)phenylcarbamate2×HCID 66612096HCID 66612096, compound

Product 1

HCID 666121101-(5-(3-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-5-chloropyridin-2-ylamino)pyridin-2-yl)-3-(4-(2-methoxyethoxy)phenyl)ureaYield 83.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N5-(3-(4-(bis(4-methoxyb enzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-5-chloropyridin-2-yl)pyridine-2,5-diamine (Example 4, step 2, 0.158 g, 0.277 mmol) and 4-nitrophenyl 4-(2-methoxyethoxy)phenylcarbamate (0.118 g, 0.354 mmol) in DCM (3 mL) was stirred at rt for 3 days. Et3N (0.20 mL) was added followed by 4-nitrophenyl 4-(2-methoxyethoxy)phenylcarbamate (0.142 g, 0.428 mmol). The reaction mixture was stirred at rt for 2 h. The yellow solid was collected and washed with DCM to give 0.176 g of crude 1-(5-(3-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-5-chloropyridin-2-ylamino)pyridin-2-yl)-3-(4-(2-methoxyethoxy)phenyl)urea, which was taken into the next step without further purification.

Workup

  1. stirringThe reaction mixture was stirred at rt for 2 h
  2. customThe yellow solid was collected
  3. washwashed with DCM

Sources & evidence

ORD record
ord-fb139886e1fa4071bb99a5b77f4e9780
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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