Triethylamine → HCID 136377201, compound

HRID 624549Notes

Reaction equation

HRID 624549 reaction equation
[CH3:1][C:2]1[S:24][C:5]2[NH:6][C:7]3[CH:21]=[CH:20][C:19]([CH2:22][NH2:23])=[CH:18][C:8]=3[N:9]=[C:10]([N:11]3[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)[C:4]=2[CH:3]=1.C(N(CC)CC)C.[CH3:32][O:33][C:34](=[O:47])[CH2:35][CH2:36][C:37](ON1C(=O)CCC1=O)=[O:38]>ClCCl>[CH3:32][O:33][C:34](=[O:47])[CH2:35][CH2:36][C:37]([NH:23][CH2:22][C:19]1[CH:20]=[CH:21][C:7]2[NH:6][C:5]3[S:24][C:2]([CH3:1])=[CH:3][C:4]=3[C:10]([N:11]3[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)=[N:9][C:8]=2[CH:18]=1)=[O:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13798889Methyl 4-[(2,5-dioxopyrrolidin-1-yl)oxy]-4-oxobutanoateHCID 136252345HCID 136252345, compound

Product 1

HCID 136377201HCID 136377201, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-methyl-4-(4-methylpiperazin-1-yl)-10H-benzo[b]thieno[2,3-e][1,4]diazepin-7-yl)methanamine, prepared as described in Example 3, (40 mg, 0.12 mmol) in dichloromethane (2 mL) was added triethylamine (0.030 mL, 0.22 mmol) and succinic acid 2,5-dioxo-pyrrolidin-1-yl ester methyl ester, prepared as described in the previous step, (31 mg, 0.13 mmol). The solution was stirred at room temperature for 1 hour and concentrated. The crude was loaded onto a silica column, eluted with 3-5% methanol/dichloromethane containing ammonium hydroxide to give the title compound as a yellow solid. LC-MS: m/z 456 (M+1).

Workup

  1. customprepared
  2. concentrationconcentrated
  3. washeluted with 3-5% methanol/dichloromethane
  4. additioncontaining ammonium hydroxide

Sources & evidence

ORD record
ord-dfd471df5be44800a31d58c5daf4ac0b
Source dataset
uspto-grants-2016_04
Patent number
US09303041B2

Reaction notes

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