N-BOC-ethylenediamine → HCID 67270305, compound

HRID 1804535Notes

Reaction equation

HRID 1804535 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:25]([F:28])([F:27])[F:26])[CH:23]=3)[NH:18][C:17]2=[O:29])[C:5]2[C:6](=[N:8][N:9]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[CH:10]=2)[N:7]=1.C([NH:37][CH2:38][CH2:39][NH2:40])(OC(C)(C)C)=O>C(O)C>[ClH:1].[NH2:37][CH2:38][CH2:39][NH:40][C:2]1[N:3]=[C:4]([CH:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:25]([F:27])([F:26])[F:28])[CH:23]=3)[NH:18][C:17]2=[O:29])[C:5]2[C:6](=[N:8][N:9]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[CH:10]=2)[N:7]=1

Participants

4

Reactant 2

HCID 187201N-BOC-ethylenediamineHCID 24880899HCID 24880899, compound

Product 1

HCID 67270305HCID 67270305, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of Example 153 (63 mg, 0.15 mmol), N-BOC-ethylenediamine (0.24 gm, 1.5 mmol), and ethanol (1 mL) were heated in a microwave at 130° C. for 10 minutes. The reaction was cooled to room temperature and a precipitate formed. The solid was filtered, washed with ethanol and ethyl ether to give 56 mg (68%) of the intermediate. Next, the material was stirred in 4N HCl in 1,4-dioxane (2 mL). After 1 hour the reaction was concentrated. The solid was treated with ether and filtered to give 35 mg (70%) of Example 252. Example 252: 1HNMR (400 MHz, DMSO-d6) δ 12.0 (s, 1H), 10.3 (s, 1H), 9.5 (s, 1H), 8.6 (s, 1H), 8.0 (m, 2H), 7.4 (m, 2H), 6.9 (m, 1H), 4.8 (m, 1H), 3.7 (m, 2H), 3.2 (m, 2H), 1.6-2.2 (m, 8H); MS (m/e) 446 (M+1); HPLC (99%) purity, retention time 3.917 minutes—Method C; mp 290-293° C.

Workup

  1. customa precipitate formed
  2. filtrationThe solid was filtered
  3. washwashed with ethanol and ethyl ether

Sources & evidence

ORD record
ord-51009e7c2d6a4fc6a78717fc5d9b5851
Source dataset
uspto-grants-2013_01
Patent number
US08354414B2

Reaction notes

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