Carbon Tetrachloride → HCID 11994257, compound

HRID 226255Notes

Reaction equation

HRID 226255 reaction equation
O[CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]1[CH2:9][CH2:10][NH:11][C:12]1[C:25]2[C:24](=[O:26])[C:23]3[C:18](=[C:19]([OH:28])[CH:20]=[CH:21][C:22]=3[OH:27])[C:17](=[O:29])[C:16]=2[C:15]([NH:30][CH2:31][CH2:32][N:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]2CO)=[CH:14][CH:13]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:60]([Cl:64])(Cl)(Cl)Cl.C(Cl)[Cl:66]>>[Cl:66][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]1[CH2:9][CH2:10][NH:11][C:12]1[C:25]2[C:24](=[O:26])[C:23]3[C:18](=[C:19]([OH:28])[CH:20]=[CH:21][C:22]=3[OH:27])[C:17](=[O:29])[C:16]=2[C:15]([NH:30][CH2:31][CH2:32][N:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]2[CH2:60][Cl:64])=[CH:14][CH:13]=1

Participants

5

Reactant 4

HCID 5943Carbon TetrachlorideHCID 6344DichloromethaneHCID 11776TriphenylphosphineHCID 444177421,4-Dihydroxy-5,8-bis[[2-[2-(hydroxymethyl)-1-piperidinyl]ethyl]amino]-9,10-anthracenedione

Product 1

HCID 11994257HCID 11994257, compoundYield 78%

Procedure

The method follows that of CAQ39 using HAQ105 (60 mg, 0.109 mmol), Ph3P (171.5 mg, 0.654 mmol), CCl4 (190 μL, 1.96 mmol) and dry CH2Cl2 (5 mL). The reaction was stopped after 5 hours of reflux. The product (CAQ190M) was afforded as a dark blue powder (49.8 mg, 78%). M.p. decompose>300° C.; δH (250 MHz; DMSO); 1.5-1.65 (m, 4H, 4×ring-H), 1.75-2.15 (m, 10H, 10×ring-H), 3.4-3.8 (m, 8H, 2×HNCH2CH2N and 4×ring-H), 4-4.1 (q, 4H, 2×HNCH2CH2N), 4.15 (2×d, 4H, 2×NCHCH2Cl) 7.2 (s, 2H, C(2)H and C(3)H), 7.65 (s, 2H, C(6)H and C(7)H), 10.45 (t, 2H, C(1)NH and C(4)NH), and 13.45 (s, 2H, C(5)OH, C(8)OH); δC (62.9 MHz; DMSO), 26.11, 37.05, 42.78, 50.78, 51.83, 60.32, 62.26, 108.41, 114.33, 125.00, 126.56, 145.93, 154.69, 184.28; FAB MS, m/z(M+H)+589.

Workup

  1. temperatureof reflux

Sources & evidence

ORD record
ord-d6e4d86662964129a42221ca729de5f6
Source dataset
uspto-grants-2009_07
Patent number
US07557215B2

Reaction notes

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