N-Boc-N-methylethylenediamine → HCID 67269617, compound

HRID 1804538Notes

Reaction equation

HRID 1804538 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH:5]2[C:12]1[C:13]2[C:14](=[N:19][N:20]([CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:21]=2)[N:15]=[C:16]([Cl:18])[N:17]=1.[C:27]([N:34](C)[CH2:35][CH2:36][NH2:37])(OC(C)(C)C)=O>C(O)C>[ClH:18].[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH:5]2[C:12]1[C:13]2[C:14](=[N:19][N:20]([CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:21]=2)[N:15]=[C:16]([NH:37][CH2:36][CH2:35][NH:34][CH3:27])[N:17]=1

Participants

4

Reactant 2

HCID 2756424N-Boc-N-methylethylenediamineHCID 86616708HCID 86616708, compound

Product 1

HCID 67269617HCID 67269617, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 5-Bromo-3-(6-chloro-2-cyclopentyl-2-H-pyrazolo[3,4-d]pyrimidin-4-yl)-1,3-dihydro-indol-2-one (50 mg, 0.115 mmol) (Example 182), N′-BOC-N′-methylethylenediamine (200 mg, 1.15 mmol) and ethanol (2 mL) were heated to 130° C. in a microwave for 10 minutes. The reaction was concentrated, treated with ethyl ether and filtered to give 36 mg (55%) of the product. The product was dissolved in 4N HCl in dioxane (3 mL) and stirred at rt for 1 hr. The reaction was concentrated, treated with acetone and filtered. The solid was washed with acetone, ethyl ether and pumped dry to give 9 mg (28%) of Example 378. Example 378: 1H NMR (400 MHz, TFA-d) δ 8.9 (s, 1H), 8.1 (s, 1H), 7.7 (d, 1H), 7.4 (d, 1H), 5.1 (m, 1H), 4.3 (m, 2H), 4.0 (m, 4H), 3.1 (m, 3H), 2.1-2.8 (m, 8H); MS (m/e) 470 (M+1); HPLC (99%) purity, retention time 3.040 minutes—Method C; mp 201-204° C.

Workup

  1. concentrationThe reaction was concentrated
  2. additiontreated with ethyl ether
  3. filtrationfiltered

Sources & evidence

ORD record
ord-a38ab1607ae54d7fa1ce2640d262eadb
Source dataset
uspto-grants-2013_01
Patent number
US08354414B2

Reaction notes

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